UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM N-CSR
CERTIFIED SHAREHOLDER REPORT OF REGISTERED MANAGEMENT INVESTMENT COMPANIES
Investment Company Act file number 811-21982
Guggenheim Strategic Opportunities Fund
(Exact name of registrant as specified in charter)
227 West Monroe Street, Chicago, IL 60606
(Address of principal executive offices) (Zip code)
Amy J. Lee
227 West Monroe Street, Chicago, IL 60606
(Name and address of agent for service)
Registrant’s telephone number, including area code: (312) 827-0100
Date of fiscal year end: May 31
Date of reporting period: June 1, 2019 – November 30, 2019


Item 1.  Reports to Stockholders.
The registrant’s semi-annual report transmitted to shareholders pursuant to Rule 30e-1 under the Investment Company Act of 1940, as amended (the “Investment Company Act”), is as follows:



 

GUGGENHEIMINVESTMENTS.COM/GOF
... YOUR WINDOW TO THE LATEST, MOST UP-TO-DATE INFORMATION ABOUT GUGGENHEIM STRATEGIC OPPORTUNITIES FUND
The shareholder report you are reading right now is just the beginning of the story. Online at guggenheiminvestments.com/gof, you will find:
Daily, weekly and monthly data on share prices, net asset values, distributions and more
Portfolio overviews and performance analyses
Announcements, press releases and special notices
Fund and adviser contact information
Guggenheim Partners Investment Management, LLC and Guggenheim Funds Investment Advisors, LLC are continually updating and expanding shareholder information services on the Fund’s website in an ongoing effort to provide you with the most current information about how your Fund’s assets are managed and the results of our efforts. It is just one more small way we are working to keep you better informed about your investment in the Fund.


 
   
(Unaudited) 
November 30, 2019 
 
DEAR SHAREHOLDER
We thank you for your investment in the Guggenheim Strategic Opportunities Fund (the “Fund”). This report covers the Fund’s performance for the six-month period ended November 30, 2019.
The Fund’s investment objective is to maximize total return through a combination of current income and capital appreciation. The Fund pursues a relative value-based investment philosophy. The Fund’s sub-adviser seeks to combine a credit-managed fixed-income portfolio with access to a diversified pool of alternative investments and equity strategies.
All Fund returns cited—whether based on net asset value (“NAV”) or market price—assume the reinvestment of all distributions. For the six-month period ended November 30, 2019, the Fund provided a total return based on market price of 2.76% and a total return based on NAV of 1.66%. As of November 30, 2019, the Fund’s market price of $19.36 represented a premium of 13.08% to its NAV of $17.12. NAV return includes the deduction of management fees, operating expenses, and all other Fund expenses.
Past performance is not a guarantee of future results. All NAV returns include the deduction of management fees, operating expenses, and all other Fund expenses. The market price of the Fund’s shares fluctuates from time to time, and it may be higher or lower than the Fund’s NAV.
From June 2019 through November 2019, the Fund paid a monthly distribution of $0.1821 per share. The latest distribution represents an annualized distribution rate of 11.29% based on the Fund’s closing market price of $19.36 on November 30, 2019. The Fund’s distribution rate is not constant and the amount of distributions, when declared by the Fund’s Board of Trustees, is subject to change based on the performance of the Fund. Please see the Distributions to Shareholders & Annualized Distribution Rate on page 16, and Note 2(f) on page 64 for more information on distributions for the period.
Guggenheim Funds Investment Advisors, LLC (the “Adviser”) serves as the investment adviser to the Fund. Guggenheim Partners Investment Management, LLC (“GPIM” or the “Sub-Adviser”) serves as the Fund’s investment sub-adviser and is responsible for the management of the Fund’s portfolio of investments. Each of the Adviser and the Sub-Adviser is an affiliate of Guggenheim Partners, LLC (“Guggenheim”), a global diversified financial services firm.
We encourage shareholders to consider the opportunity to reinvest their distributions from the Fund through the Dividend Reinvestment Plan (“DRIP”), which is described in detail on page 89 of this report. When shares trade at a discount to NAV, the DRIP takes advantage of the discount by reinvesting the monthly dividend distribution in common shares of the Fund purchased in the market at a price less than NAV. Conversely, when the market price of the Fund’s common shares is at a premium above NAV, the DRIP reinvests participants’ dividends in newly-issued common shares at the greater of NAV per share or 95% of the market price per share. The DRIP provides a cost-effective means to accumulate additional shares and enjoy the benefits of compounding returns over time. Since the Fund endeavors to maintain a stable monthly distribution, the DRIP effectively provides an income averaging technique

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 3


   
DEAR SHAREHOLDER (Unaudited) continued 
November 30, 2019 
 
which causes shareholders to accumulate a larger number of Fund shares when the market price is depressed than when the price is higher.
To learn more about the Fund’s performance and investment strategy, we encourage you to read the Economic and Market Overview and the Questions & Answers sections of this report, which begin on page 5. You’ll find information on Guggenheim’s investment philosophy, views on the economy and market environment, and detailed information about the factors that impacted the Fund’s performance.
We appreciate your investment and look forward to serving your investment needs in the future. For the most up-to-date information on your investment, please visit the Fund’s website at guggenheiminvestments.com/gof.

Sincerely,

Guggenheim Funds Investment Advisors, LLC
Guggenheim Strategic Opportunities Fund

December 31, 2019

4 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
ECONOMIC AND MARKET OVERVIEW (Unaudited) 
November 30, 2019 
 
U.S. real gross domestic product (“GDP”) growth held roughly steady at a 2.1% annualized rate in the third quarter of 2019 versus 2.0% in the second quarter. The data showed a moderation in government spending and personal consumption expenditure growth, which came in at a 3.1% annualized rate after an unsustainably strong 4.6% reading in the prior quarter. However, this was largely offset by a smaller drag from inventories and net exports.
Despite the pullback in consumer spending growth, the U.S. household sector has remained a bright spot, as clouds have gathered over the global economy. The manufacturing sector has borne the brunt of the escalation in U.S.-China tariffs, while also contending with headwinds in the form of U.S. dollar appreciation and weakness in foreign demand. Beyond the U.S., the trade conflict and China’s ongoing financial deleveraging have detracted from global trade volumes, which are contracting on a year-over-year basis for the first time since 2009. The global trade recession has weighed on GDP growth in economies that are particularly trade- and investment-oriented. Real GDP growth in China slowed to 6.0% year over year in the third quarter, the slowest pace in several decades, while German GDP grew by just 0.3% annualized in the third quarter of 2019 after contracting by 1.0% in the prior quarter.
The good news is that the manufacturing sector represents only 11.0% of U.S. GDP and 8.4% of non-farm payrolls. We see encouraging signs of an upturn in goods production, which a tentative U.S.-China trade truce should support. Meanwhile, growth in the much larger services sector has moderated, with real personal spending on services having softened over the past year. Also noteworthy to us was the decline in the employment diffusion index of the IHS Markit purchasing managers index (“PMI”) for services, which fell to 47.5 in October before rebounding in November and December. Global PMIs also showed a sequential improvement in labor market conditions in November.
Fiscal policy is estimated to have boosted U.S. real GDP growth by about 0.6% in 2019. This substantial fiscal support should fade in 2020, resulting in no contribution to growth (a shift in the growth impulse). We expect the U.S. Federal Reserve (the “Fed”) to remain on hold in the near term, with monetary policymakers having indicated that the bar is high for further rate changes. This message has since been reinforced by the Fed’s senior leadership, who have noted that “monetary policy is in a good place.” The recent rally in stocks and bear steepening (widening caused by long-term interest rates increasing at a faster rate than short-term rates) of the yield curve suggests that markets agree.
The Fed’s mid-cycle adjustment appears to have successfully staved off recession. The expansion will likely continue in the near term with the help of global monetary easing efforts that are helping to drive risk assets higher. Year-to-date performance across different asset classes shows rates and cyclical equities both delivering better returns than credit, although the Fed’s easing will likely allow risks to build in certain areas of the credit markets. For now, we continue to focus on income and capital preservation.
The opinions and forecasts expressed may not actually come to pass. This information is subject to change at any time, based on market and other conditions, and should not be construed as a recommendation of any specific security or strategy.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 5


   
QUESTIONS & ANSWERS (Unaudited) 
November 30, 2019 
 
Guggenheim Strategic Opportunities Fund (“Fund”) is managed by a team of seasoned professionals at Guggenheim Partners Investment Management, LLC (“GPIM”). This team includes B. Scott Minerd, Chairman of Guggenheim Investments and Global Chief Investment Officer; Anne B. Walsh, CFA, JD, Senior Managing Director and Chief Investment Officer, Fixed Income; Steven H. Brown, CFA, Senior Managing Director and Portfolio Manager; and Adam Bloch, Managing Director and Portfolio Manager. In the following interview, the investment team discusses the market environment and the Fund’s performance for the six-month period ended November 30, 2019.
What is the Fund’s investment objective and how is it pursued?
The Fund seeks to maximize total return through a combination of current income and capital appreciation. The Fund pursues a relative value-based investment philosophy, which utilizes quantitative and qualitative analysis.
The Fund seeks to combine a credit-managed fixed-income portfolio with access to a diversified pool of alternative investments and equity strategies. The Fund seeks to achieve its investment objective by investing in a wide range of fixed-income and other debt and senior-equity securities (“Income Securities”) selected from a variety of credit qualities and sectors, including, but not limited to, corporate bonds, loans and loan participations, structured finance investments, U.S. government and agency securities, mezzanine and preferred securities and convertible securities, and in common stocks, limited liability company interests, trust certificates, and other equity investments (“Common Equity Securities”), exposure to which is obtained primarily by investing in exchange-traded funds (“ETFs”) that Guggenheim believes offer attractive yield and/or capital appreciation potential, including employing a strategy of writing (selling) covered call and put options on such equities. Guggenheim believes the volatility of the Fund can be reduced by diversifying across a large number of sectors and securities, some of which historically have not been highly correlated to one another.
Under normal market conditions:
The Fund may invest without limitation in fixed-income securities rated below investment grade (commonly referred to as “junk bonds”); the Fund may invest in below-investment grade income securities of any rating;
The Fund may invest up to 20% of its total assets in non-U.S. dollar denominated fixed-income securities of corporate and governmental issuers located outside the U.S., including up to 10% of total assets in fixed-income securities of issuers located in emerging markets;

6 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
The Fund may invest up to 50% of its total assets in common equity securities, and the Fund may invest in ETFs or other investment funds that track equity market indices and/or through derivative instruments that replicate the economic characteristics of exposure to Common Equity Securities; and
The Fund may invest up to 30% of its total assets in investment funds that primarily hold (directly or indirectly) investments in which the Fund may invest directly, of which amount up to 30% of the Fund’s total assets may be invested in investment funds that are registered as investment companies under the Investment Company Act of 1940 (the “1940 Act”) to the extent permitted by applicable law and related interpretations of the staff of the U.S. Securities and Exchange Commission.
Guggenheim’s process for determining whether to buy a security is a collaborative effort between various groups including: (i) economic research, which focus on key economic themes and trends, regional and country-specific analysis, and assessments of event-risk and policy impacts on asset prices, (ii) the Portfolio Construction Group, which utilize proprietary portfolio construction and risk modeling tools to determine allocation of assets among a variety of sectors, (iii) its Sector Specialists, who are responsible for identifying investment opportunities in particular securities within these sectors, including the structuring of certain securities directly with the issuers or with investment banks and dealers involved in the origination of such securities, and (iv) portfolio managers, who determine which securities best fit the Fund based on the Fund’s investment objective and top-down sector allocations. In managing the Fund, Guggenheim uses a process for selecting securities for purchase and sale that is based on intensive credit research and involves extensive due diligence on each issuer, region and sector. Guggenheim also considers macroeconomic outlook and geopolitical issues.
The Fund may use financial leverage to finance the purchase of additional securities. Although financial leverage may create an opportunity for increased return for shareholders, it also results in additional risks and can magnify the effect of any losses. There is no assurance that the strategy will be successful. If income and gains earned on securities purchased with the financial leverage proceeds are greater than the cost of the financial leverage, common shareholders’ return will be greater than if financial leverage had not been used. Conversely, if the income or gains from the securities purchased with the proceeds of financial leverage are less than the cost of the financial leverage, common shareholders’ return will be less than if financial leverage had not been used.
How did the Fund perform for the six months ended November 30, 2019?
All Fund returns cited—whether based on net asset value (“NAV”) or market price—assume the reinvestment of all distributions. For the six-month period ended November 30, 2019, the Fund provided a total return based on market price of 2.76% and a total return based on NAV of 1.66%. As

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 7


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
of November 30, 2019, the Fund’s market price of $19.36 represented a premium of 13.08% to its NAV of $17.12. As of May 31, 2019, the Fund’s market price of $19.96 represented a premium of 11.45% to its NAV of $17.91. NAV return includes the deduction of management fees, operating expenses, and all other Fund expenses. The market value of the Fund’s shares fluctuates from time to time and may be higher or lower than the Fund’s NAV. Past performance is not a guarantee of future results.
What were the Fund’s distributions?
From June 2019 through November 2019, the Fund paid a monthly distribution of $0.1821 per share. The latest distribution represents an annualized distribution rate of 11.29% based on the Fund’s closing market price of $19.36 on November 30, 2019. The Fund’s distribution rate is not constant and the amount of distributions, when declared by the Fund’s Board of Trustees, is subject to change based on the performance of the Fund. Please see the Distributions to Shareholders & Annualized Distribution Rate on page 16, and Note 2(f) on page 64 for more information on distributions for the period.
   
How did other markets perform in this environment for the six-month period ended November 30, 2019? 
 
Index 
Total Return 
Bloomberg Barclays U.S. Aggregate Bond Index 
3.81% 
Bloomberg Barclays U.S. Aggregate Bond 1-3 Year Index 
1.61% 
Bloomberg Barclays U.S. Corporate High Yield Index 
4.27% 
Credit Suisse Leveraged Loan Index 
1.21% 
ICE Bank of America Merrill Lynch Asset Backed Security Master BBB-AA Index 
1.95% 
S&P 500 Index 
15.26% 
 
Discuss performance over the period.
During the period, the Fund saw positive performance primarily attributable to the portfolio’s carry. Carry refers to the income received from portfolio investments over a defined period. Spreads widened over the period, although many sectors remain near cycle tights. While trade uncertainty and recession fears persisted over the period, in November optimism of an initial US-China trade agreement, anticipation of a strong holiday sales seasons, and better than expected jobless claims fueled bullish sentiment leading to a rally in risk assets.
Interest rates across the Treasury curve fell between 30 and 80 basis points over the period, which aided in the Fund’s performance.
Over the period, the Fund added taxable and tax-free municipal closed-end funds to take advantage of attractive yields and discounted share prices relative to their NAVs.

8 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
Bank loans, which constituted 41% of the Fund at period’s end, generated a positive total return despite spreads widening over the period, as associated price declines were more than offset by income earned. The Fund increased its allocation to the asset class over the period as spread widening presented opportunities to selectively add exposure.
Collateralized Loan Obligations (“CLOs”), which constituted 11% of the Fund at period’s end, detracted from performance as spread widening in CLO equity outpaced income earned. We continue to favor senior CLOs with short spread durations, as they offer a compelling spread pickup to similarly rated corporates while providing defensive positioning.
Non-Agency Residential Mortgage-Backed Securities (“non-Agency RMBS”), which constituted 10% of the Fund at period’s end, were also positive contributors as lower rates and improving credit fundamentals drove higher prepayments for discounted dollar price holdings. Limited home inventory and improving labor market conditions should support home prices and mortgage credit performance. Pre-crisis RMBS investment has benefited from a supply shortfall caused by ongoing paydowns and limited new issuance.
Asset Backed Securities (“ABS”) (not including CLO’s), which constituted 7% of the Fund at period’s end, performed well generating positive total returns as the investor base for esoteric structured credit, including aircraft securitization and other commercial ABS, continues to grow.
The Fund’s modest exposure to investment grade credit contributed to performance.
What was the impact of derivatives on Fund performance?
The Fund uses derivatives for its covered call strategy and for various hedging purposes, such as currency forward contracts to fully hedge exchange rate risk in the purchase of government securities of foreign countries. It also uses various derivatives to obtain exposure to indexes that track various equity market sectors.
Index futures contributed to performance for the period. Returns from the covered call allocation was roughly flat over the period. The allocation was reduced in May in line with our broader plan to help protect the portfolio and shareholders from future drawdowns.
The Fund also maintained a credit hedge via credit default swaps to reduce portfolio spread duration and help protect shareholders from a drawdown. With investment grade corporate spreads marginally tighter, the credit hedge detracted from performance over the period.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 9


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
Discuss the Fund’s approach to duration.
Although the Fund has no set policy regarding portfolio duration or maturity, the Fund maintained a generally low-duration throughout the period.
Discuss the Fund’s use of leverage.
The Fund employed no leverage during the period.
Index Definitions
Indices are unmanaged and reflect no expenses. It is not possible to invest directly in an index.
The Bloomberg Barclays U.S. Aggregate Bond Index is a broad-based flagship benchmark that measures the investment grade, U.S. dollar-denominated, fixed-rate taxable bond market, including U.S. Treasuries, government-related and corporate securities, mortgage-backed securities or “MBS” (agency fixed-rate and hybrid adjustable-rate mortgage, or “ARM”, pass-throughs), ABS, and commercial mortgage-backed securities (“CMBS”) (agency and non-agency).
The Bloomberg Barclays U.S. Aggregate Bond 1-3 Year Index measures the performance of publicly issued investment grade corporate, U.S. Treasury and government agency securities with remaining maturities of one to three years.
The Bloomberg Barclays U.S. Corporate High Yield Index measures the U.S. dollar-denominated, high yield, fixed-rate corporate bond market. Securities are classified as high yield if the middle rating of Moody’s, Fitch, and S&P is Ba1/BB +/BB + or below.
The Credit Suisse Leveraged Loan Index is an index designed to mirror the investable universe of the U.S.-dollar-denominated leveraged loan market.
The ICE Bank of America Merrill Lynch Asset Backed Security Master BBB-AA Index is a subset of the ICE BofA/ML U.S. Fixed Rate Asset Backed Securities Index including all securities rated AA1 through BBB3, inclusive.
The Standard & Poor’s 500 (“S&P 500”) Index is a capitalization-weighted index of 500 stocks designed to measure the performance of the broad economy, representing all major industries and is considered a representation of the U.S. stock market.

10 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
Risks and Other Considerations
Investing involves risk, including the possible loss of principal and fluctuation of value. The views expressed in this report reflect those of the portfolio managers only through the report period as stated on the cover. These views are expressed for informational purposes only and are subject to change at any time, based on market and other conditions, and may not come to pass. These views may differ from views of other investment professionals at Guggenheim and should not be construed as research, investment advice or a recommendation of any kind regarding the fund or any issuer or security, do not constitute a solicitation to buy or sell any security and should not be considered specific legal, investment or tax advice. The information provided does not take into account the specific objectives, financial situation or particular needs of any specific investor.
The views expressed in this report may also include forward looking statements that involve risk and uncertainty, and there is no guarantee that any predictions will come to pass. Actual results or events may differ materially from those projected, estimated, assumed or anticipated in any such forward-looking statements. Important factors that could result in such differences, in addition to the other factors noted with such forward-looking statements, include general economic conditions such as inflation, recession and interest rates.
There can be no assurance that the Fund will achieve its investment objectives or that any investment strategies or techniques discussed herein will be effective. The value of the Fund will fluctuate with the value of the underlying securities. Historically, closed-end funds often trade at a discount to their net asset value.
As part of its investment strategy, the Fund utilizes short sales and a variety of derivative instruments. These investments involve, to varying degrees, elements of market risk and risks in excess of amounts recognized in the Statement of Assets and Liabilities. Valuation and accounting treatment of these instruments can be found under Significant Accounting Policies in Note 2 of these Notes to Financial Statements.
Performance data quoted represents past performance, which is no guarantee of future results and current performance may be lower or higher than the figures shown.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 11


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2019 
 
Please see guggenheiminvestments.com/gof for a detailed discussion of the Fund’s risks and considerations.
This material is not intended as a recommendation or as investment advice of any kind, including in connection with rollovers, transfers, and distributions. Such material is not provided in a fiduciary capacity, may not be relied upon for or in connection with the making of investment decisions, and does not constitute a solicitation of an offer to buy or sell securities. All content has been provided for informational or educational purposes only and is not intended to be and should not be construed as legal or tax advice and/or a legal opinion. Always consult a financial, tax and/or legal professional regarding your specific situation.

12 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
FUND SUMMARY (Unaudited) 
November 30, 2019 
 
   
Fund Statistics 
 
Share Price 
$19.36 
Net Asset Value 
$17.12 
Premium to NAV 
13.08% 
Net Assets ($000) 
$675,796 
 
           
AVERAGE ANNUAL TOTAL RETURNS FOR THE
PERIOD ENDED NOVEMBER 30, 2019
 
Six month 
 
 
 
 
 
(non- 
One 
Three 
Five 
Ten 
 
annualized) 
Year 
Year 
Year 
Year 
Guggenheim Strategic Opportunities Fund 
 
 
 
 
NAV 
1.66% 
4.74% 
8.92% 
9.02% 
12.34% 
Market 
2.76% 
8.66% 
12.07% 
9.37% 
13.48% 
 
Performance data quoted represents past performance, which is no guarantee of future results and current performance may be lower or higher than the figures shown. All NAV returns include the deduction of management fees, operating expenses and all other Fund expenses. The deduction of taxes that a shareholder would pay on Fund distributions or the sale of Fund shares is not reflected in the total returns. For the most recent month-end performance figures, please visit guggenheiminvestments.com/gof. The investment return and principal value of an investment will fluctuate with changes in market conditions and other factors so that an investor’s shares, when sold, may be worth more or less than their original cost.
   
Ten Largest Holdings 
(% of Total Net Assets) 
Morgan Stanley Finance LLC, 1.50% 
1.9% 
Government of Japan, 01/10/20 
1.5% 
BlackRock Taxable Municipal Bond Trust 
1.0% 
Nuveen Taxable Municipal Income Fund 
0.9% 
Federative Republic of Brazil, 01/01/20 
0.9% 
State of Israel, 1.00%, 04/30/21 
0.9% 
TSGE, 6.25% 
0.8% 
LSTAR Securities Investment Limited, 3.20% 
0.7% 
Lehman XS Trust Series, 1.89% 
0.7% 
Golub Capital Partners CLO Ltd., 3.99% 
0.7% 
Top Ten Total 
10.0 % 
 
“Ten Largest Holdings” excludes any temporary cash or derivative investments.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 13


   
FUND SUMMARY (Unaudited) continued 
November 30, 2019 
 
   
Portfolio Breakdown 
% of Net Assets 
Investments 
 
Senior Floating Rate Interests 
41.0% 
Asset-Backed Securities 
17.4% 
Corporate Bonds 
17.2% 
Collateralized Mortgage Obligations 
11.2% 
Foreign Government Debt 
6.4% 
Closed-End Funds 
4.3% 
Money Market Fund 
1.3% 
Other 
2.0% 
Total Investments 
100.8% 
Corporate Bonds Sold Short 
-0.4% 
Put Options Written 
0.0%* 
Other Assets & Liabilities, net 
-0.4% 
Net Assets 
100.0% 
 
Holdings diversification and holdings are subject to change daily. For more information, please visit guggenheiminvestments.com/gof. The above summaries are provided for informational purposes only and should not be viewed as recommendations. Past performance does not guarantee future results.
*    Less than 0.1%.


14 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
FUND SUMMARY (Unaudited) continued 
November 30, 2019 
 
Portfolio Composition by Quality Rating1
   
 
% of Total 
Rating 
Investments 
Investments 
 
AAA 
0.3% 
AA 
2.3% 
12.1% 
BBB 
10.5% 
BB 
12.8% 
31.2% 
CCC 
5.2% 
CC 
5.5% 
0.7% 
0.1% 
NR2 
14.3% 
Other Instruments 
 
Other 
5.0% 
Total Investments 
100.0% 
 
1
Source: BlackRock Solutions. Credit quality ratings are measured on a scale that generally ranges from AAA (highest) to D (lowest). All rated securities have been rated by Moody’s, Standard & Poor’s (“S&P”), or Fitch, each of which is a Nationally Recognized Statistical Rating Organization (“NRSRO”). For purposes of this presentation, when ratings are available from more than one agency, the highest rating is used. Guggenheim Investments has converted Moody’s and Fitch ratings to the equivalent S&P rating. Security ratings are determined at the time of purchase and may change thereafter
2
NR securities do not necessarily indicate low credit quality.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 15


   
FUND SUMMARY (Unaudited) continued 
November 30, 2019 
 







Portfolio breakdown is subject to change daily. For more information, please visit guggenheiminvestments.com/gof. The above summaries are provided for informational purposes only and should not be viewed as recommendations. Past performance does not guarantee future results. All or a portion of the above distributions may be characterized as a return of capital. For the calendar year ended December 31, 2019, 63% of the distributions were characterized as return of capital and 37% of the distributions were characterized as ordinary income. The final determination of the tax character of the distributions paid by the Fund in 2019 will be reported to shareholders in January 2020.

16 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) 
 
November 30, 2019 
 
 

 
 
Shares 
Value 
 
COMMON STOCKS– 0.3% 
 
 
Consumer, Non-cyclical – 0.2% 
 
 
Chef Holdings, Inc.*,†††,1 
4,789 
$ 580,618 
ATD New Holdings, Inc.*,†† 
13,571 
339,275 
Cengage Learning Holdings II, Inc.*,†† 
11,126 
116,823 
Targus Group International Equity, Inc.*,†††,1,2 
12,989 
22,683 
Total Consumer, Non-cyclical 
 
1,059,399 
 
Utilities – 0.1% 
 
 
TexGen Power LLC*,†† 
22,219 
988,745 
 
Energy – 0.0% 
 
 
SandRidge Energy, Inc.*,17 
39,565 
130,169 
Titan Energy LLC*,17 
9,603 
279 
Total Energy 
 
130,448 
 
Technology – 0.0% 
 
 
Qlik Technologies, Inc. – Class A*,†††,1 
56 
72,131 
Qlik Technologies, Inc. – Class B*,†††,1 
13,812 
– 
Total Technology 
 
72,131 
 
Industrial – 0.0% 
 
 
BP Holdco LLC*,†††,1,2 
55,076 
19,447 
Vector Phoenix Holdings, LP*,†††,1 
55,076 
4,609 
Total Industrial 
 
24,056 
Total Common Stocks 
 
 
(Cost $3,387,298) 
 
2,274,779 
 
PREFERRED STOCKS†† – 0.4% 
 
 
Financial – 0.3% 
 
 
Public Storage 5.40% 
41,000 
1,053,700 
AmTrust Financial Services, Inc. 7.75% 
35,100 
621,270 
AgriBank FCB 6.88% 
4,000 
428,000 
AmTrust Financial Services, Inc. 7.50% 
3,410 
59,504 
AmTrust Financial Services, Inc. 7.63% 
2,940 
51,715 
AmTrust Financial Services, Inc. 7.25% 
1,685 
29,993 
Total Financial 
 
2,244,182 
 
Industrial – 0.1% 
 
 
Lytx Holdings, LLC *,†††,1 
591 
591,396 
Total Preferred Stocks 
 
 
(Cost $2,562,893) 
 
2,835,578 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 17


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Shares 
Value 
 
WARRANTS††† – 0.0% 
 
 
Lytx, Inc.*,1 
26 
$ 131 
Total Warrants 
 
 
(Cost $–) 
 
131 
 
CLOSED-END FUNDS– 4.3% 
 
 
BlackRock Taxable Municipal Bond Trust 
281,604 
6,721,887 
Nuveen Taxable Municipal Income Fund 
281,945 
6,104,109 
Nuveen AMT-Free Municipal Credit Income Fund 
285,719 
4,614,362 
Invesco Municipal Opportunity Trust 
221,815 
2,752,724 
Invesco Trust for Investment Grade Municipals 
201,581 
2,554,031 
Invesco Municipal Trust 
178,403 
2,185,437 
Invesco Advantage Municipal Income Trust II 
156,732 
1,741,293 
BlackRock Municipal Income Trust 
106,147 
1,477,566 
Nuveen AMT-Free Quality Municipal Income Fund 
28,110 
396,351 
Nuveen Quality Municipal Income Fund 
23,225 
335,369 
BlackRock MuniVest Fund, Inc. 
23,028 
207,713 
Total Closed-End Funds 
 
 
(Cost $29,700,933) 
 
29,090,842 
 
MONEY MARKET FUND– 1.3% 
 
 
Dreyfus Treasury Securities Cash Management Fund — Institutional Shares 1.52%5 
9,049,257 
9,049,257 
Total Money Market Fund 
 
 
(Cost $9,049,257) 
 
9,049,257 

 
Face 
 
 
Amount~ 
 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% 
 
 
Consumer, Cyclical – 9.1% 
 
 
EG Finco Ltd. 
 
 
6.10% (3 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 02/07/25 
3,007,380 
2,924,045 
8.75% (3 Month EURIBOR + 7.75%, Rate Floor: 8.75%) due 04/20/26 
EUR 249,505 
274,249 
Titan AcquisitionCo New Zealand Ltd. 
 
 
6.35% (3 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 05/01/26 
2,793,000 
2,799,284 
Accuride Corp. 
 
 
7.35% (3 Month USD LIBOR + 5.25%, Rate Floor: 6.25%) due 11/17/23 
3,376,702 
2,701,361 
1-800 Contacts 
 
 
5.20% (3 Month USD LIBOR + 3.00%, Rate Floor: 4.00%) due 01/22/23 
2,583,276 
2,554,860 
CH Holding Corp. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 02/05/26 
1,995,000 
2,001,484 
BGIS (BIFM CA Buyer, Inc.) 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 06/01/26 
1,745,625 
1,743,443 
Shields Health Solutions Holdings LLC 
 
 
6.70% (1 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 08/19/26††† 
1,750,000 
1,732,500 
 
See notes to financial statements.

18 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Consumer, Cyclical – 9.1% (continued) 
 
 
PT Intermediate Holdings III LLC 
 
 
7.49% (3 Month USD LIBOR + 5.50%, Rate Floor: 6.50%) due 10/15/25††† 
1,700,000 
$ 1,691,500 
Packers Sanitation Services, Inc. 
 
 
5.57% (3 Month USD LIBOR + 3.25%, Rate Floor: 4.25%) due 12/04/24 
1,697,975 
1,680,469 
Midas Intermediate Holdco II LLC 
 
 
4.85% (3 Month USD LIBOR + 2.75%, Rate Floor: 3.75%) due 08/18/21 
1,773,908 
1,670,808 
Power Solutions (Panther) 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 04/30/26 
1,650,000 
1,648,977 
World Triathlon Corp. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 08/15/26 
1,650,000 
1,637,625 
BCPE Empire Holdings, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 06/11/26 
1,627,025 
1,612,789 
ERM 
 
 
5.85% (3 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 07/10/26 
1,596,000 
1,596,287 
BBB Industries, LLC 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 08/01/25 
1,634,492 
1,580,358 
AVSC Holding Corp. 
 
 
6.49% (3 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 10/15/26 
1,250,000 
1,225,787 
5.14% (1 Month USD LIBOR + 3.25% and 3 Month 
 
 
USD LIBOR + 3.25%, Rate Floor: 4.25%) due 03/03/25 
323,925 
314,107 
Touchtunes Interactive Network 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 05/28/21 
1,553,684 
1,538,147 
OEConnection LLC 
 
 
5.71% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 09/25/26 
1,552,814 
1,536,634 
CPI Acquisition, Inc. 
 
 
6.71% (3 Month USD LIBOR + 4.50%, Rate Floor: 6.50%) due 08/17/22 
2,021,782 
1,521,957 
K & N Parent, Inc. 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 10/20/23††† 
1,937,936 
1,453,452 
SHO Holding I Corp. 
 
 
6.93% (3 Month USD LIBOR + 5.00%, Rate Floor: 6.00%) due 10/27/22 
1,295,810 
1,140,313 
5.87% (1 Month USD LIBOR + 4.00% and 3 Month USD 
 
 
LIBOR + 4.00%, Rate Floor: 4.00%) due 10/27/21†††,1 
334,000 
298,930 
Comet Bidco Ltd. 
 
 
6.91% (1 Month USD LIBOR + 5.00% and 3 Month USD 
 
 
LIBOR + 5.00%, Rate Floor: 6.00%) due 09/30/24 
1,477,612 
1,427,743 
IBC Capital Ltd. 
 
 
5.90% (3 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 09/11/23 
1,433,861 
1,423,107 
EnTrans International, LLC 
 
 
7.70% (1 Month USD LIBOR + 6.00%, Rate Floor: 6.00%) due 11/01/24††† 
1,415,625 
1,366,078 
Apro LLC 
 
 
5.84% (3 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 11/14/26 
1,320,000 
1,323,300 
Blue Nile, Inc. 
 
 
8.41% (3 Month USD LIBOR + 6.50%, Rate Floor: 7.50%) due 02/17/23 
1,775,000 
1,273,563 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 19


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Consumer, Cyclical – 9.1% (continued) 
 
 
Alexander Mann 
 
 
6.70% (1 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 06/16/25††† 
1,300,000 
$ 1,254,500 
WESCO 
 
 
6.36% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 06/14/24†††,1 
1,161,618 
1,157,242 
SMG US Midco 2, Inc. 
 
 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 01/23/25 
985,000 
984,389 
8.70% (1 Month USD LIBOR + 7.00%, Rate Floor: 7.00%) due 01/23/26 
125,000 
125,625 
Galls LLC 
 
 
8.09% (2 Month USD LIBOR + 6.25%, Rate Floor: 7.25%) due 01/31/25†††,1 
863,446 
856,267 
8.42% (1 Month USD LIBOR + 6.25% and Commercial Prime Lending 
 
 
Rate + 5.25%, Rate Floor: 7.25%) due 01/31/24†††,1 
113,195 
102,945 
8.08% (1 Month USD LIBOR + 6.25% and 2 Month USD LIBOR + 6.25%, 
 
 
Rate Floor: 7.25%) due 01/31/25†††,1 
95,533 
94,738 
Atkins Nutritionals, Inc. 
 
 
5.73% (3 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 07/08/24††† 
1,000,000 
1,005,000 
Cast & Crew Payroll LLC 
 
 
5.71% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 02/09/26 
995,000 
998,114 
AT Home Holding III 
 
 
5.43% (3 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 06/03/22 
1,098,497 
988,648 
Prime Security Services Borrower LLC (ADT) 
 
 
5.03% (1 Month USD LIBOR + 3.25%, Rate Floor: 4.25%) due 09/23/26 
1,000,000 
988,500 
Aimbridge Acquisition Co., Inc. 
 
 
5.46% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 02/02/26††† 
747,500 
751,238 
Nellson Nutraceutical 
 
 
6.35% (3 Month USD LIBOR + 4.25% and Commercial Prime Lending 
 
 
Rate + 3.25%, Rate Floor: 5.25%) due 12/23/21††† 
818,227 
736,404 
Zephyr Bidco Ltd. 
 
 
8.21% (1 Month GBP LIBOR + 7.50%, Rate Floor: 7.50%) due 07/23/26 
GBP 570,000 
727,615 
Checkers Drive-In Restaurants, Inc. 
 
 
6.16% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 04/25/24 
1,002,861 
652,692 
NES Global Talent 
 
 
7.43% (3 Month USD LIBOR + 5.50%, Rate Floor: 6.50%) due 05/11/23 
618,987 
615,892 
Sotheby’s 
 
 
7.27% (1 Month USD LIBOR + 5.50%, Rate Floor: 6.50%) due 01/15/27 
560,141 
544,911 
American Tire Distributors, Inc. 
 
 
7.72% (1 Month USD LIBOR + 6.00%, Rate Floor: 7.00%) due 09/01/23 
425,232 
418,216 
9.20% (1 Month USD LIBOR + 7.50%, Rate Floor: 8.50%) due 09/02/24 
82,865 
72,299 
Outcomes Group Holdings, Inc. 
 
 
5.41% (1 Month USD LIBOR + 3.50% and 3 Month USD LIBOR + 3.50%, 
 
 
Rate Floor: 3.50%) due 10/24/25 
498,244 
490,357 
Belk, Inc . 
 
 
8.80% (3 Month USD LIBOR + 6.75%, Rate Floor: 7.75%) due 07/31/25 
647,386 
482,995 
 
See notes to financial statements.

20 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Consumer, Cyclical – 9.1% (continued) 
 
 
Drive Chassis (DCLI) 
 
 
10.26% (3 Month USD LIBOR + 8.25%, Rate Floor: 8.25%) due 04/10/26††† 
500,000 
$ 450,000 
Leslie’s Poolmart, Inc. 
 
 
5.34% (2 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 08/16/23 
461,279 
431,296 
Truck Hero, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 04/22/24 
436,131 
407,420 
Mavis Tire Express Services Corp. 
 
 
4.95% (1 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 03/20/25 
272,929 
257,691 
Argo Merchants 
 
 
5.85% (3 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 12/06/24 
148,896 
147,034 
SP PF Buyer LLC 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 12/22/25 
150,000 
135,300 
Petco Animal Supplies, Inc. 
 
 
5.18% (3 Month USD LIBOR + 3.25%, Rate Floor: 4.25%) due 01/26/23 
98,465 
77,604 
Total Consumer, Cyclical 
 
61,648,089 
 
Technology – 7.7% 
 
 
TIBCO Software, Inc. 
 
 
5.78% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 06/30/26 
3,250,000 
3,258,125 
Cologix Holdings, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 03/20/24 
3,150,000 
3,050,586 
Planview, Inc. 
 
 
6.95% (1 Month USD LIBOR + 5.25%, Rate Floor: 6.25%) due 01/27/23†††,1 
1,955,000 
1,955,000 
11.45% (1 Month USD LIBOR + 9.75%, Rate Floor: 10.75%) due 07/27/23†††,1 
900,000 
908,865 
Emerald TopCo, Inc. (Press Ganey) 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 07/24/26 
2,300,000 
2,288,086 
Datix Bidco Ltd. 
 
 
6.43% (6 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 04/28/25†††,1 
2,001,644 
1,986,246 
9.68% (6 Month USD LIBOR + 7.75%, Rate Floor: 7.75%) due 04/27/26†††,1 
300,111 
297,551 
GlobalFoundries, Inc. 
 
 
5.88% (2 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 06/05/26 
2,344,125 
2,250,360 
LANDesk Group, Inc. 
 
 
6.01% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 01/20/24 
2,216,349 
2,199,727 
Ministry Brands LLC 
 
 
5.86% (2 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 12/02/22††† 
2,173,665 
2,162,796 
II-VI Inc. 
 
 
5.21% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 09/24/26 
2,000,000 
2,001,260 
Upland Software, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 08/06/26 
2,000,000 
1,993,760 
Cvent, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 11/29/24 
1,970,000 
1,928,137 
EIG Investors Corp. 
 
 
5.67% (1 Month USD LIBOR + 3.75% and 3 Month USD LIBOR + 3.75%, 
 
 
Rate Floor: 4.75%) due 02/09/23 
2,006,300 
1,885,922 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 21


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Technology – 7.7% (continued) 
 
 
Brave Parent Holdings, Inc. 
 
 
5.93% (3 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 04/18/25 
1,876,250 
$ 1,805,891 
Dun & Bradstreet 
 
 
6.70% (1 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 02/06/26 
1,750,000 
1,758,750 
MRI Software LLC 
 
 
7.46% (1 Month USD LIBOR + 5.75%, Rate Floor: 6.75%) due 06/30/23 
1,685,649 
1,668,793 
7.66% (2 Month USD LIBOR + 5.75%, Rate Floor: 6.75%) due 06/30/23 
63,803 
62,905 
Park Place Technologies LLC 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 03/29/25 
1,071,485 
1,057,202 
9.70% (1 Month USD LIBOR + 8.00%, Rate Floor: 9.00%) due 03/30/26 
680,723 
670,512 
Project Boost Purchaser LLC 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 06/01/26 
1,700,000 
1,683,714 
Aston FinCo S.A.R.L. 
 
 
6.26% (3 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 10/09/26 
1,700,000 
1,683,000 
Misys Ltd. 
 
 
5.70% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 06/13/24 
1,696,804 
1,657,573 
Navicure, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 10/22/26 
1,541,667 
1,536,857 
24-7 Intouch, Inc. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 08/25/25 
1,485,000 
1,425,600 
Refinitiv (Financial & Risk Us Holdings, Inc.) 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 10/01/25 
1,389,500 
1,397,601 
Transact Holdings, Inc. 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 4.75%) due 04/30/26††† 
1,350,000 
1,316,250 
Lytx, Inc. 
 
 
8.45% (1 Month USD LIBOR + 6.75%, Rate Floor: 7.75%) due 08/31/23†††,1 
1,136,582 
1,119,000 
Optiv, Inc. 
 
 
4.95% (1 Month USD LIBOR + 3.25%, Rate Floor: 4.25%) due 02/01/24 
1,255,059 
1,027,579 
Aspect Software, Inc. 
 
 
7.21% (3 Month USD LIBOR + 5.00%, Rate Floor: 6.00%) due 01/15/24 
1,017,555 
933,607 
Greenway Health LLC 
 
 
5.85% (3 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 02/16/24 
984,887 
861,776 
Informatica LLC 
 
 
4.95% (1 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 08/05/22 
795,938 
796,224 
S2P Acquisition Borrower, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 08/14/26 
680,000 
676,811 
Apttus Corp. 
 
 
4.84% (3 Month USD LIBOR + 2.75%, Rate Floor: 2.75%) due 10/02/21†††,1 
425,000 
423,660 
Project Accelerate Parent, LLC 
 
 
6.01% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 01/02/25 
234,904 
232,555 
Peak 10 Holding Corp. 
 
 
5.60% (3 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 08/01/24 
246,231 
197,231 
Ping Identity Corp. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 01/24/25 
101,813 
101,686 
 
See notes to financial statements.

22 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Technology – 7.7% (continued) 
 
 
Targus Group International, Inc. 
 
 
due 05/24/16*,†††,1,2,11 
155,450 
$ – 
Total Technology 
 
52,261,198 
 
Industrial – 7.5% 
 
 
Alion Science & Technology Corp. 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 08/19/21 
3,324,205 
3,324,205 
Tronair Parent, Inc. 
 
 
6.66% (3 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 09/08/23††† 
3,119,797 
2,807,817 
Dynasty Acquisition Co. 
 
 
6.10% (3 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 04/06/26 
2,750,000 
2,758,167 
American Bath Group LLC 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 09/29/23 
2,681,038 
2,649,214 
Capstone Logistics 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 10/07/21 
2,613,814 
2,574,607 
ILPEA Parent, Inc. 
 
 
6.46% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 03/02/23 
2,514,976 
2,489,826 
WP CPP Holdings LLC 
 
 
5.68% (1 Month USD LIBOR + 3.75% and 3 Month USD LIBOR + 3.75%, 
 
 
Rate Floor: 4.75%) due 04/30/25 
2,356,200 
2,322,813 
Tank Holdings Corp. 
 
 
6.46% (1 Month USD LIBOR + 4.00% and 12 Month USD LIBOR + 4.00% 
 
 
and 3 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 03/26/26 
2,000,000 
2,000,000 
STS Operating, Inc. (SunSource) 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 12/11/24 
2,053,493 
1,997,022 
Sundyne Us Purchaser, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 05/15/26 
1,888,889 
1,887,718 
Foundation Building Materials Holding Company LLC 
 
 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 08/13/25 
1,736,875 
1,743,388 
NA Rail Hold Co LLC (Patriot) 
 
 
7.22% (3 Month USD LIBOR + 5.25%, Rate Floor: 5.25%) due 10/19/26††† 
1,700,000 
1,712,750 
Bioplan / Arcade 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 09/23/21 
1,853,228 
1,630,841 
API Holdings III Corp. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 05/11/26 
1,596,000 
1,544,130 
Transcendia Holdings, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 05/30/24 
1,960,088 
1,398,189 
Anchor Packaging LLC 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 07/20/26 
1,353,846 
1,331,846 
National Technical 
 
 
8.03% (1 Month USD LIBOR + 6.25%, Rate Floor: 7.25%) due 06/12/21†††,1 
1,373,523 
1,328,884 
Avison Young (Canada), Inc. 
 
 
6.98% (3 Month USD LIBOR + 5.00% and 2 Month USD LIBOR + 5.00%, 
 
 
Rate Floor: 5.00%) due 01/31/26 
1,290,250 
1,263,374 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 23


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Industrial – 7.5% (continued) 
 
 
Charter Nex US, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 05/16/24 
1,197,000 
$ 1,196,749 
Savage Enterprises LLC 
 
 
5.77% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 08/01/25 
1,063,636 
1,073,517 
Diversitech Holdings, Inc. 
 
 
9.60% (3 Month USD LIBOR + 7.50%, Rate Floor: 8.50%) due 06/02/25††† 
1,000,000 
970,000 
5.10% (3 Month USD LIBOR + 3.00%, Rate Floor: 4.00%) due 06/03/24 
99,745 
97,418 
Duran, Inc. 
 
 
6.41% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.00%) due 12/20/24 
548,505 
537,535 
6.26% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.00%) due 03/29/24 
500,285 
490,279 
Bhi Investments LLC 
 
 
10.95% (3 Month USD LIBOR + 8.75%, Rate Floor: 9.75%) due 02/28/25†††,1 
1,000,000 
987,500 
Fortis Solutions Group LLC 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 12/15/23†††,1 
582,944 
582,944 
6.27% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 12/15/23†††,1 
210,494 
210,494 
6.25% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 12/15/23†††,1 
193,249 
193,249 
Hillman Group, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 05/30/25 
989,975 
941,714 
ProAmpac PG Borrower LLC 
 
 
10.40% (3 Month USD LIBOR + 8.50%, Rate Floor: 9.50%) due 11/18/24††† 
1,000,000 
915,000 
SLR Consulting Ltd. 
 
 
5.72% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 06/23/25†††,1 
793,980 
776,901 
5.71% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 05/23/25†††,1 
82,947 
81,162 
5.71% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 06/23/25†††,1 
GBP 39,120 
49,503 
Pelican Products, Inc. 
 
 
5.27% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 05/01/25††† 
987,500 
901,094 
YAK MAT (YAK ACCESS LLC) 
 
 
11.72% (1 Month USD LIBOR + 10.00%, Rate Floor: 10.00%) due 07/10/26 
1,000,000 
853,750 
Thermon Group Holdings, Inc. 
 
 
5.53% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 10/30/24 
709,339 
710,226 
TricorBraun Holdings, Inc. 
 
 
5.86% (3 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 11/30/23 
598,463 
587,241 
BWAY Holding Co. 
 
 
5.23% (3 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 04/03/24 
497,836 
487,755 
Dimora Brands, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 08/24/24 
486,563 
471,358 
Titan Acquisition Ltd. (Husky) 
 
 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 03/28/25 
298,737 
285,500 
Hayward Industries, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 08/05/24 
261,866 
256,956 
KUEHG Corp. (KinderCare) 
 
 
5.85% (3 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 02/21/25 
99,747 
98,833 
Total Industrial 
 
50,521,469 
 
See notes to financial statements.

24 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Consumer, Non-cyclical – 6.1% 
 
 
WIRB – Copernicus Group, Inc. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 08/15/22††† 
3,614,836 
$ 3,605,799 
Springs Window Fashions 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 06/15/25 
1,786,383 
1,757,354 
10.20% (1 Month USD LIBOR + 8.50%, Rate Floor: 8.50%) due 06/15/26 
1,350,000 
1,272,375 
Endo Luxembourg Finance Co. 
 
 
6.00% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.00%) due 04/29/24 
2,256,197 
2,074,144 
Civitas Solutions, Inc. 
 
 
5.96% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 03/09/26 
1,990,585 
1,993,909 
Immucor, Inc. 
 
 
7.10% (3 Month USD LIBOR + 5.00%, Rate Floor: 6.00%) due 06/15/21 
1,955,000 
1,942,175 
PlayPower, Inc. 
 
 
7.60% (3 Month USD LIBOR + 5.50%, Rate Floor: 5.50%) due 05/08/26††† 
1,845,375 
1,817,694 
Snacking Investments US LLC (Arnott’s) 
 
 
due 10/15/26 
1,700,000 
1,696,821 
CPI Holdco LLC 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 11/04/26††† 
1,700,000 
1,695,750 
MDVIP LLC 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 11/14/24 
1,706,055 
1,695,392 
Arctic Glacier Group Holdings, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 03/20/24 
1,772,602 
1,673,638 
Cambrex Corp. 
 
 
due 11/20/26 
1,700,000 
1,670,250 
Diamond (BC) B.V. 
 
 
4.93% (2 Month USD LIBOR + 3.00% and 3 Month USD LIBOR + 3.00%, 
 
 
Rate Floor: 3.00%) due 09/06/24 
1,748,106 
1,658,079 
ScribeAmerica Intermediate Holdco LLC (Healthchannels) 
 
 
6.27% (1 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 04/03/25 
1,628,230 
1,595,665 
Confluent Health LLC 
 
 
7.10% (3 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 06/24/26††† 
1,596,000 
1,572,060 
California Cryobank 
 
 
6.10% (3 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 08/06/25††† 
1,436,617 
1,415,067 
BCPE Eagle Buyer LLC 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 03/18/24 
1,463,970 
1,376,132 
Hearthside Group Holdings LLC 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 05/23/25 
1,439,125 
1,341,265 
Smart Foodservice (Sage Borrowco LLC) 
 
 
6.44% (1 Month USD LIBOR + 4.75%, Rate Floor: 4.75%) due 06/19/26††† 
1,296,750 
1,301,613 
Tecbid US, Inc. 
 
 
6.35% (3 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 07/25/24††† 
988,890 
990,126 
Affordable Care Holding 
 
 
6.59% (2 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 10/24/22††† 
970,000 
943,325 
Sotera Health Holdings LLC 
 
 
5.43% (3 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 05/16/22 
897,750 
894,006 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 25


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Consumer, Non-cyclical – 6.1% (continued) 
 
 
Packaging Coordinators Midco, Inc. 
 
 
6.11% (3 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 06/30/23 
828,300 
$ 821,052 
Give and Go Prepared Foods Corp. 
 
 
6.35% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 07/29/23 
823,200 
773,808 
CTI Foods Holding Co. LLC 
 
 
8.91% (3 Month USD LIBOR + 7.00%, Rate Floor: 8.00%) due 05/03/24††† 
467,357 
469,694 
10.91% (3 Month USD LIBOR + 9.00%, Rate Floor: 10.00%) due 05/03/24††† 
190,424 
178,999 
Certara, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 08/15/24 
613,005 
603,810 
Hoffmaster Group, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 11/21/23††† 
438,775 
429,999 
Moran Foods LLC 
 
 
due 12/05/2311 
1,191,324 
422,920 
Kar Nut Products Company 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 03/31/23†††,1 
373,023 
370,431 
Recess Holdings, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 09/30/24 
299,237 
294,748 
Sierra Acquisition, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 11/11/24 
297,733 
294,011 
Affordable Care Holdings Corp. 
 
 
6.59% (2 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 10/24/22††† 
240,567 
233,951 
Sterigenics-Norion Holdings 
 
 
4.93% (3 Month USD LIBOR + 3.00%, Rate Floor: 4.00%) due 05/15/22 
224,425 
222,928 
Examworks Group, Inc. 
 
 
4.95% (1 Month USD LIBOR + 3.25%, Rate Floor: 4.25%) due 07/27/23 
99,489 
99,862 
Total Consumer, Non-cyclical 
 
41,198,852 
 
Basic Materials – 3.1% 
 
 
ICP Industrial, Inc. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 11/03/23††† 
2,460,415 
2,448,113 
American Rock Salt Company LLC 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 03/21/25 
1,906,739 
1,909,122 
PetroChoice Holdings 
 
 
6.93% (2 Month USD LIBOR + 5.00% and 3 Month USD LIBOR + 5.00%, 
 
 
Rate Floor: 6.00%) due 08/19/22 
2,024,474 
1,862,516 
PeroxyChem Holdings LP 
 
 
7.06% (6 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 10/01/24††† 
1,700,000 
1,693,625 
GrafTech Finance, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.50%) due 02/12/25 
1,664,194 
1,622,590 
Niacet Corp. 
 
 
6.20% (1 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 02/01/24††† 
1,609,644 
1,601,596 
Big River Steel LLC 
 
 
7.10% (3 Month USD LIBOR + 5.00%, Rate Floor: 6.00%) due 08/23/23 
1,532,025 
1,513,840 
DCG Acquisition Corp. 
 
 
6.51% (3 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 09/30/26 
1,506,667 
1,491,600 
 
See notes to financial statements.

26 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Basic Materials – 3.1% (continued) 
 
 
Pregis TopCo Corp. 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 07/31/26 
1,450,000 
$ 1,419,187 
Ascend Performance Materials Operations LLC 
 
 
7.35% (1 Month USD LIBOR + 5.25%, Rate Floor: 6.25%) due 08/27/26 
1,000,000 
1,000,000 
US Salt LLC 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 4.75%) due 01/16/26 
995,000 
996,244 
LTI Holdings, Inc. 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 09/06/25 
990,000 
842,203 
Niacet B.V. 
 
 
5.50% (1 Month EURIBOR + 4.50%, Rate Floor: 5.50%) due 02/01/24 
EUR 757,480 
830,515 
Vectra Co. 
 
 
4.95% (1 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 03/08/25 
547,859 
536,732 
ASP Chromaflo Dutch I B.V. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 11/20/23 
449,961 
442,649 
ASP Chromaflo Intermediate Holdings, Inc. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 11/20/23 
346,039 
340,416 
Noranda Aluminum Acquisition Corp. 
 
 
8.00% (3 Month USD LIBOR + 4.25%, Rate Floor: 5.75%) due 02/28/19†††,11 
517,932 
25,897 
Total Basic Materials 
 
20,576,845 
 
Financial – 2.7% 
 
 
Nexus Buyer LLC 
 
 
5.51% (3 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 11/09/26 
1,700,000 
1,708,500 
National Financial Partners Corp. 
 
 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 01/08/24 
1,699,232 
1,677,992 
Teneo Holdings LLC 
 
 
7.02% (1 Month USD LIBOR + 5.25%, Rate Floor: 6.25%) due 07/11/25 
1,750,000 
1,627,500 
Virtu Financial, Inc. 
 
 
6.04% (3 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 03/01/26 
1,608,228 
1,605,220 
Aretec Group, Inc. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 4.25%) due 10/01/25 
1,687,250 
1,589,390 
Jefferies Finance LLC 
 
 
5.56% (3 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 06/03/26 
1,546,125 
1,529,380 
Claros Mortgage Trust, Inc. 
 
 
5.01% (1 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 08/10/26 
1,500,000 
1,500,000 
StepStone Group LP 
 
 
5.84% (2 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 03/27/25††† 
1,477,500 
1,470,113 
Situs AMC Holdings Corp. 
 
 
6.45% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 06/28/25††† 
1,466,595 
1,444,596 
Alliant Holdings Intermediate LLC 
 
 
5.02% (1 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 05/09/25 
997,500 
991,764 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 05/09/25 
198,992 
196,754 
HUB International Ltd. 
 
 
5.90% (3 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 04/25/25 
1,000,000 
1,002,040 
4.69% (3 Month USD LIBOR + 2.75%, Rate Floor: 2.75%) due 04/25/25 
99,747 
98,305 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 27


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Financial – 2.7% (continued) 
 
 
USI, Inc. 
 
 
due 12/02/26 
600,000 
$ 598,998 
5.10% (3 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 05/16/24 
248,731 
245,363 
Jane Street Group LLC 
 
 
4.70% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 08/25/22 
497,487 
494,169 
Northstar Financial Services LLC 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 4.25%) due 05/26/25 
392,341 
382,858 
Assetmark Financial Holdings, Inc. 
 
 
5.35% (3 Month USD LIBOR + 3.25%, Rate Floor: 3.25%) due 11/14/25 
358,875 
360,669 
Total Financial 
 
18,523,611 
 
Communications – 2.7% 
 
 
Trader Interactive 
 
 
8.20% (1 Month USD LIBOR + 6.50%, Rate Floor: 7.50%) due 06/17/24†††,1 
2,711,211 
2,680,679 
Conterra Ultra Broadband Holdings, Inc. 
 
 
6.21% (1 Month USD LIBOR + 4.50%, Rate Floor: 4.50%) due 04/30/26 
1,995,000 
1,990,013 
Market Track LLC 
 
 
6.18% (2 Month USD LIBOR + 4.25% and 3 Month USD LIBOR + 4.25%, 
 
 
Rate Floor: 5.25%) due 06/05/24††† 
2,101,625 
1,870,446 
Flight Bidco, Inc. 
 
 
9.20% (1 Month USD LIBOR + 7.50%, Rate Floor: 7.50%) due 07/23/26 
1,300,000 
1,283,750 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 07/23/25 
447,739 
443,821 
STV Group, Inc. 
 
 
due 11/22/26 
1,700,000 
1,687,250 
ProQuest, LLC 
 
 
5.20% (1 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 10/23/26 
1,650,000 
1,654,125 
Liberty Cablevision Of Puerto Rico LLC 
 
 
6.77% (1 Month USD LIBOR + 5.00%, Rate Floor: 5.00%) due 10/15/26 
1,200,000 
1,209,300 
Resource Label Group LLC 
 
 
6.60% (3 Month USD LIBOR + 4.50%, Rate Floor: 5.50%) due 05/26/23 
1,322,865 
1,177,350 
Internet Brands, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 09/13/24 
1,047,140 
1,043,213 
SFR Group S.A. 
 
 
5.77% (1 Month USD LIBOR + 4.00%, Rate Floor: 4.00%) due 08/14/26 
997,481 
989,062 
Imagine Print Solutions LLC 
 
 
6.46% (1 Month USD LIBOR + 4.75%, Rate Floor: 5.75%) due 06/21/22 
1,950,000 
776,743 
Houghton Mifflin Co. 
 
 
due 11/22/24 
700,000 
675,500 
Mcgraw-Hill Global Education Holdings LLC 
 
 
5.70% (1 Month USD LIBOR + 4.00%, Rate Floor: 5.00%) due 05/04/22 
483,281 
440,255 
Cengage Learning Acquisitions, Inc. 
 
 
5.95% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 06/07/23 
188,446 
172,087 
Total Communications 
 
18,093,594 
 
See notes to financial statements.

28 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
SENIOR FLOATING RATE INTERESTS††,7 – 41.0% (continued) 
 
 
Utilities – 1.5% 
 
 
Oregon Clean Energy LLC 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 4.75%) due 03/02/26 
2,462,173 
$ 2,459,095 
Panda Power 
 
 
8.60% (3 Month USD LIBOR + 6.50%, Rate Floor: 7.50%) due 08/21/20 
2,350,698 
1,899,035 
UGI Energy Services, Inc. 
 
 
5.45% (1 Month USD LIBOR + 3.75%, Rate Floor: 3.75%) due 08/13/26 
1,645,875 
1,651,027 
Franklin Energy (KAMC Holdings, Inc.) 
 
 
5.91% (2 Month USD LIBOR + 4.00% and 3 Month USD LIBOR + 4.00%, 
 
 
Rate Floor: 4.00%) due 08/14/26††† 
1,650,000 
1,645,875 
Carroll County Energy LLC 
 
 
5.60% (3 Month USD LIBOR + 3.50%, Rate Floor: 3.50%) due 02/16/26 
1,544,683 
1,544,683 
EIF Channelview Cogeneration LLC 
 
 
5.96% (1 Month USD LIBOR + 4.25%, Rate Floor: 5.25%) due 05/03/25 
865,904 
870,450 
Total Utilities 
 
10,070,165 
 
Energy – 0.6% 
 
 
SeaPort Financing LLC 
 
 
7.21% (1 Month USD LIBOR + 5.50%, Rate Floor: 5.50%) due 10/31/25††† 
1,488,750 
1,458,975 
Summit Midstream Partners, LP 
 
 
7.70% (1 Month USD LIBOR + 6.00%, Rate Floor: 7.00%) due 05/13/22 
1,122,648 
1,081,481 
Permian Production Partners LLC 
 
 
10.90% (1 Month USD LIBOR + 6.00%, Rate Floor: 7.00%) due 05/20/24†††,11 
1,805,000 
902,500 
Gavilan Resources LLC 
 
 
7.70% (1 Month USD LIBOR + 6.00%, Rate Floor: 7.00%) due 03/01/24 
990,000 
346,500 
Total Energy 
 
3,789,456 
Total Senior Floating Rate Interests 
 
 
(Cost $286,776,449) 
 
276,683,279 
 
ASSET-BACKED SECURITIES†† – 17.4% 
 
 
Collateralized Loan Obligations – 10.7% 
 
 
Golub Capital Partners CLO Ltd. 
 
 
2018-36A, 3.99% (3 Month USD LIBOR + 2.10%, Rate Floor: 0.00%) due 02/05/316,7 
5,000,000 
4,619,232 
2018-39A, 4.17% (3 Month USD LIBOR + 2.20%, Rate Floor: 2.20%) due 10/20/286,7 
2,500,000 
2,438,119 
2018-25A, 3.79% (3 Month USD LIBOR + 1.90%, Rate Floor: 1.90%) due 05/05/306,7 
2,500,000 
2,427,193 
2017-16A, 4.94% (3 Month USD LIBOR + 3.00%, Rate Floor: 0.00%) due 07/25/296,7 
1,500,000 
1,458,314 
Diamond CLO Ltd. 
 
 
2018-1A, 5.65% (3 Month USD LIBOR + 3.70%, Rate Floor: 3.70%) due 07/22/306,7 
3,000,000 
2,925,603 
2018-1A, 4.55% (3 Month USD LIBOR + 2.60%, Rate Floor: 2.60%) due 07/22/306,7 
2,500,000 
2,432,110 
Mountain Hawk II CLO Ltd. 
 
 
2018-2A, 4.32% (3 Month USD LIBOR + 2.35%, Rate Floor: 0.00%) due 07/20/246,7 
3,000,000 
2,986,904 
2013-2A, 5.12% (3 Month USD LIBOR + 3.15%, Rate Floor: 0.00%) due 07/22/246,7 
1,750,000 
1,744,429 
Fortress Credit Opportunities IX CLO Ltd. 
 
 
2017-9A, 4.56% (3 Month USD LIBOR + 2.65%, Rate Floor: 0.00%) due 11/15/296,7 
4,000,000 
3,868,256 
Marathon CRE Ltd. 
 
 
2018-FL1, 4.77% (1 Month USD LIBOR + 3.00%, Rate Floor: 3.00%) due 06/15/286,7 
3,000,000 
2,999,991 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 29


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
ASSET-BACKED SECURITIES†† – 17.4% (continued) 
 
 
Collateralized Loan Obligations – 10.7% (continued) 
 
 
FDF I Ltd. 
 
 
2015-1A, 6.88% due 11/12/306 
2,000,000 
$ 1,995,711 
2015-1A, 7.50% due 11/12/308 
1,000,000 
989,247 
FDF II Ltd. 
 
 
2016-2A, 7.70% due 05/12/318 
3,000,000 
2,974,679 
Dryden 50 Senior Loan Fund 
 
 
2017-50A, due 07/15/308,9 
3,555,000 
2,441,887 
Denali Capital CLO XI Ltd. 
 
 
2018-1A, 4.12% (3 Month USD LIBOR + 2.15%, Rate Floor: 0.00%) due 10/20/286,7 
2,400,000 
2,341,290 
Newstar Commercial Loan Funding LLC 
 
 
2017-1A, 7.26% (3 Month USD LIBOR + 5.10%, Rate Floor: 0.00%) due 03/20/276,7 
2,000,000 
2,001,327 
2017-1A, 5.66% (3 Month USD LIBOR + 3.50%, Rate Floor: 0.00%) due 03/20/276,7 
250,000 
250,142 
Hull Street CLO Ltd. 
 
 
2017-1A, 4.70% (3 Month USD LIBOR + 2.70%, Rate Floor: 0.00%) due 10/18/266,7 
2,200,000 
2,200,623 
Avery Point VI CLO Ltd. 
 
 
2018-6A, 3.89% (3 Month USD LIBOR + 2.00%, Rate Floor: 0.00%) due 08/05/276,7 
2,000,000 
1,958,290 
MP CLO VIII Ltd. 
 
 
2018-2A, 3.84% (3 Month USD LIBOR + 1.90%, Rate Floor: 0.00%) due 10/28/276,7 
2,000,000 
1,939,620 
DRSLF 
 
 
due 01/15/319 
2,998,799 
1,855,696 
Exantas Capital Corporation Ltd. 
 
 
2018-RSO6, 4.26% (1 Month USD LIBOR + 2.50%, Rate Floor: 2.50%) due 06/15/356,7 
1,800,000 
1,802,243 
Atlas Senior Loan Fund IX Ltd. 
 
 
2018-9A, due 04/20/288,9,17 
2,600,000 
1,118,445 
2018-9A, 3.77% (3 Month USD LIBOR + 1.80%, Rate Floor: 1.80%) due 04/20/286,7 
700,000 
674,370 
Hunt CRE Ltd. 
 
 
2017-FL1, 5.07% (1 Month USD LIBOR + 3.30%, Rate Floor: 0.00%) due 08/15/346,7 
1,800,000 
1,791,045 
Cent CLO 19 Ltd. 
 
 
2013-19A, 5.23% (3 Month USD LIBOR + 3.30%, Rate Floor: 0.00%) due 10/29/256,7 
1,750,000 
1,742,576 
Avery Point II CLO Ltd. 
 
 
2013-3X COM, due 01/18/259 
2,399,940 
1,728,506 
Monroe Capital CLO Ltd. 
 
 
2017-1A, 5.55% (3 Month USD LIBOR + 3.60%, Rate Floor: 0.00%) due 10/22/266,7 
1,750,000 
1,706,484 
OHA Credit Partners IX Ltd. 
 
 
2013-9A, due 10/20/256,9 
2,000,000 
1,683,845 
Treman Park CLO Ltd. 
 
 
2015-1A, due 10/20/286,9 
2,000,000 
1,618,727 
NewStar Clarendon Fund CLO LLC 
 
 
2015-1A, 6.29% (3 Month USD LIBOR + 4.35%, Rate Floor: 0.00%) due 01/25/276,7 
1,000,000 
1,000,127 
2019-1A, 4.99% (3 Month USD LIBOR + 3.05%, Rate Floor: 0.00%) due 01/25/276,7 
550,000 
549,281 
Carlyle Global Market Strategies CLO Ltd. 
 
 
2012-3A, due 01/14/328,9 
2,600,000 
1,286,537 
Voya CLO Ltd. 
 
 
2013-1A, due 10/15/308,9 
3,000,000 
1,259,499 
 
See notes to financial statements.

30 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
ASSET-BACKED SECURITIES†† – 17.4% (continued) 
 
 
Collateralized Loan Obligations – 10.7% (continued) 
 
 
Jackson Mill CLO Ltd. 
 
 
2018-1A, 3.85% (3 Month USD LIBOR + 1.85%, Rate Floor: 1.85%) due 04/15/276,7 
1,000,000 
$ 986,203 
KVK CLO Ltd. 
 
 
2013-1A, due 01/14/288,9,17 
2,300,000 
713,389 
Dryden 41 Senior Loan Fund 
 
 
2015-41A, due 04/15/318,9 
1,250,000 
706,816 
Great Lakes CLO Ltd. 
 
 
2014-1A, due 10/15/296,9 
1,153,846 
687,049 
Dryden 37 Senior Loan Fund 
 
 
2015-37A, due 01/15/318,9 
1,050,000 
649,754 
Venture XIII CLO Ltd. 
 
 
2013-13A, due 09/10/298,9 
1,500,000 
504,949 
Babson CLO Ltd. 
 
 
2014-IA, due 07/20/258,9 
3,000,000 
433,242 
Marathon CLO V Ltd. 
 
 
2013-5A, due 11/21/278,9 
3,566,667 
349,177 
A10 Permanent Asset Financing LLC 
 
 
2017-II, 6.24% (WAC) due 06/15/51†††,1,6,7 
250,000 
267,747 
West CLO Ltd. 
 
 
2013-1A, due 11/07/258,9 
1,350,000 
200,343 
Total Collateralized Loan Obligations 
 
72,309,017 
 
Transport-Aircraft – 3.8% 
 
 
Apollo Aviation Securitization Equity Trust 
 
 
2019-2, 4.46% due 10/16/396 
3,972,400 
3,953,398 
2019-1, 4.95% due 05/15/396 
1,909,000 
1,909,354 
2018-1A, 5.44% due 01/16/386 
2,278,544 
2,322,486 
2017-1A, 5.93% due 05/16/426 
1,839,677 
1,895,620 
2016-2, 7.87% due 11/15/41 
869,902 
870,670 
2016-2, 5.93% due 11/15/41 
512,841 
521,420 
AIM Aviation Finance Ltd. 
 
 
2015-1A, 5.07% due 02/15/406 
3,598,126 
3,595,703 
AASET US Ltd. 
 
 
2018-2A, 5.43% due 11/18/386 
2,729,297 
2,771,319 
Willis Engine Securitization Trust II 
 
 
2012-A, 5.50% due 09/15/376,10 
1,995,978 
2,058,491 
KDAC Aviation Finance Ltd. 
 
 
2017-1A, 4.21% due 12/15/426 
1,599,061 
1,624,801 
Falcon Aerospace Limited 
 
 
2017-1, 6.30% due 02/15/426 
1,562,427 
1,581,727 
Stripes Aircraft Ltd. 
 
 
2013-1 A1, 5.22% due 03/20/23††† 
999,747 
987,516 
Castlelake Aircraft Securitization Trust 
 
 
due 12/31/30†††,1,12 
3,054,105 
882,010 
Turbine Engines Securitization Ltd. 
 
 
2013-1A, 6.38% due 12/13/488 
456,880 
404,367 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 31


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
ASSET-BACKED SECURITIES†† – 17.4% (continued) 
 
 
Transport-Aircraft – 3.8% (continued) 
 
 
Airplanes Pass Through Trust 
 
 
2001-1A, 2.88% (1 Month USD LIBOR + 0.55%, Rate Floor: 0.55%) due 03/15/19†††,7,8,11 
6,677,317 
$ 106,420 
Total Transport-Aircraft 
 
25,485,302 
 
Financial – 0.9% 
 
 
Madison Avenue Secured Funding Trust 
 
 
2019-1, 3.30% (1 Month USD LIBOR + 1.50%, 
 
 
Rate Floor: 1.50%) due 11/11/20†††,6,7 
3,300,000 
3,300,000 
Nassau LLC 
 
 
2019-1, 3.98% due 08/15/346 
2,103,504 
2,087,845 
NCBJ 
 
 
2015-1A, 5.88% due 07/08/22†††,1 
878,774 
911,182 
Total Financial 
 
6,299,027 
 
Whole Business – 0.9% 
 
 
TSGE 
 
 
2017-1, 6.25% due 09/25/31†††,1 
5,000,000 
5,174,539 
Wingstop Funding LLC 
 
 
2018-1, 4.97% due 12/05/486 
995,000 
1,016,572 
Total Whole Business 
 
6,191,111 
 
Insurance – 0.3% 
 
 
LTCG Securitization Issuer LLC 
 
 
2018-A, 4.59% due 06/15/486 
1,939,428 
1,956,347 
CBC Insurance Revenue Securitization LLC 
 
 
2016-1, 5.25% due 07/15/468 
340,552 
347,647 
Total Insurance 
 
2,303,994 
 
Infrastructure – 0.3% 
 
 
Secured Tenant Site Contract Revenue Notes Series 
 
 
2018-1A, 5.92% due 06/15/486 
1,953,683 
1,944,709 
 
Diversified Payment Rights – 0.2% 
 
 
Bib Merchant Voucher Receivables Ltd. 
 
 
4.18% due 04/07/28†††,1 
1,100,000 
1,146,602 
 
Collateralized Debt Obligations – 0.2% 
 
 
Anchorage Credit Funding 4 Ltd. 
 
 
2016-4A, 5.50% due 02/15/356 
1,000,000 
1,006,933 
Highland Park CDO I Ltd. 
 
 
2006-1A, 3.05% (3 Month USD LIBOR + 0.40%, Rate Floor: 0.00%) due 11/25/517,8,17 
135,089 
133,869 
Total Collateralized Debt Obligations 
 
1,140,802 
 
Transport-Container – 0.1% 
 
 
Global SC Finance II SRL 
 
 
2013-1A, 2.98% due 04/17/286 
683,333 
683,464 
 
See notes to financial statements.

32 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
ASSET-BACKED SECURITIES†† – 17.4% (continued) 
 
 
Transport-Rail – 0.0% 
 
 
Trinity Rail Leasing, LP 
 
 
2009-1A, 6.66% due 11/16/396 
151,916 
$ 174,971 
Total Asset-Backed Securities 
 
 
(Cost $127,233,459) 
 
117,678,999 
 
CORPORATE BONDS†† – 17.2% 
 
 
Financial – 7.1% 
 
 
Morgan Stanley Finance LLC 
 
 
1.50% due 10/23/29†††,4 
13,500,000 
13,122,975 
Bank of America Corp. 
 
 
6.50%3,4 
2,000,000 
2,265,000 
6.30%3,4 
1,000,000 
1,145,000 
QBE Insurance Group Ltd. 
 
 
7.50% due 11/24/434,6 
3,000,000 
3,345,000 
American Equity Investment Life Holding Co. 
 
 
5.00% due 06/15/27 
2,950,000 
3,152,420 
BBC Military Housing-Navy Northeast LLC 
 
 
6.30% due 10/15/4917 
2,800,000 
3,104,773 
Citizens Financial Group, Inc. 
 
 
5.50%3,4 
2,500,000 
2,515,625 
Macquarie Group Ltd. 
 
 
5.03% due 01/15/304,6 
2,000,000 
2,282,943 
Fort Knox Military Housing Privatization Project 
 
 
5.82% due 02/15/526 
1,918,382 
2,174,309 
Assurant, Inc. 
 
 
4.90% due 03/27/28 
1,950,000 
2,145,927 
CNB Financial Corp. 
 
 
5.75% due 10/15/264,8 
2,000,000 
2,038,855 
Atlas Mara Ltd. 
 
 
8.00% due 12/31/208 
2,200,000 
1,947,000 
Hunt Companies, Inc. 
 
 
6.25% due 02/15/266 
1,675,000 
1,658,250 
Springleaf Finance Corp. 
 
 
6.13% due 03/15/24 
1,500,000 
1,642,515 
Newmark Group, Inc. 
 
 
6.13% due 11/15/23 
1,450,000 
1,593,825 
Jefferies Finance LLC / JFIN Company-Issuer Corp. 
 
 
7.25% due 08/15/246 
1,500,000 
1,530,000 
Fort Benning Family Communities LLC 
 
 
6.09% due 01/15/516 
725,545 
860,360 
Pacific Beacon LLC 
 
 
5.63% due 07/15/516,17 
692,989 
753,328 
Fort Gordon Housing LLC 
 
 
6.32% due 05/15/516 
200,000 
239,457 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 33


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
CORPORATE BONDS†† – 17.2% (continued) 
 
 
Financial – 7.1% (continued) 
 
 
USI, Inc. 
 
 
6.88% due 05/01/256 
150,000 
$ 150,750 
Oxford Finance LLC / Oxford Finance Company-Issuer II, Inc. 
 
 
6.38% due 12/15/226 
100,000 
103,240 
Icahn Enterprises, LP / Icahn Enterprises Finance Corp. 
 
 
5.88% due 02/01/22 
50,000 
50,286 
Total Financial 
 
47,821,838 
 
Energy – 2.1% 
 
 
Hess Corp. 
 
 
5.60% due 02/15/41 
1,550,000 
1,766,801 
6.00% due 01/15/40 
1,000,000 
1,155,619 
7.13% due 03/15/33 
500,000 
627,474 
Global Partners Limited Partnership / GLP Finance Corp. 
 
 
7.00% due 08/01/276 
1,625,000 
1,698,507 
Indigo Natural Resources LLC 
 
 
6.88% due 02/15/266 
1,750,000 
1,588,125 
Husky Energy, Inc. 
 
 
4.00% due 04/15/24 
900,000 
943,347 
3.95% due 04/15/22 
600,000 
619,173 
Antero Resources Corp. 
 
 
5.63% due 06/01/23 
1,200,000 
849,000 
5.13% due 12/01/22 
370,000 
300,625 
5.38% due 11/01/21 
230,000 
212,462 
Sunoco Logistics Partners Operations, LP 
 
 
4.25% due 04/01/24 
1,000,000 
1,043,161 
American Midstream Partners Limited Partnership / American Midstream Finance Corp. 
 
 
9.50% due 12/15/216 
895,000 
841,300 
Buckeye Partners, LP 
 
 
4.35% due 10/15/24 
750,000 
745,421 
Bruin E&P Partners LLC 
 
 
8.88% due 08/01/238 
990,000 
633,600 
Basic Energy Services, Inc. 
 
 
10.75% due 10/15/238 
500,000 
357,500 
Unit Corp. 
 
 
6.63% due 05/15/21 
343,000 
176,645 
Summit Midstream Holdings LLC / Summit Midstream Finance Corp. 
 
 
5.50% due 08/15/22 
200,000 
173,000 
FLNG Liquefaction 2 LLC 
 
 
4.13% due 03/31/388 
123,288 
116,326 
Schahin II Finance Co. SPV Ltd. 
 
 
5.88% due 09/25/226,11 
1,216,133 
91,210 
Total Energy 
 
13,939,296 
 
See notes to financial statements.

34 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
CORPORATE BONDS†† – 17.2% (continued) 
 
 
Industrial – 1.9% 
 
 
Encore Capital Group, Inc. 
 
 
5.63% due 08/11/24††† 
3,800,000 
$ 3,803,158 
Great Lakes Dredge & Dock Corp. 
 
 
8.00% due 05/15/22 
1,776,000 
1,884,915 
Reynolds Group Issuer Incorporated / Reynolds Group Issuer LLC / 
 
 
Reynolds Group Issuer Luxembourg 
 
 
5.50% (3 Month USD LIBOR + 3.50%) due 07/15/216,7 
1,225,000 
1,228,062 
5.75% due 10/15/20 
436,098 
436,622 
Intertape Polymer Group, Inc. 
 
 
7.00% due 10/15/266 
1,450,000 
1,508,000 
Princess Juliana International Airport Operating Company N.V. 
 
 
5.50% due 12/20/278 
1,459,483 
1,402,855 
Grinding Media Inc. / MC Grinding Media Canada Inc. 
 
 
7.38% due 12/15/236 
1,280,000 
1,277,530 
Cleaver-Brooks, Inc. 
 
 
7.88% due 03/01/236 
950,000 
908,438 
Standard Industries, Inc. 
 
 
5.38% due 11/15/246 
400,000 
411,500 
Glenn Pool Oil & Gas Trust 
 
 
6.00% due 08/02/21††† 
338,117 
334,958 
Total Industrial 
 
13,196,038 
 
Consumer, Cyclical – 1.8% 
 
 
HP Communities LLC 
 
 
6.16% due 09/15/536,17 
1,000,000 
1,263,371 
6.82% due 09/15/536,17 
956,522 
1,147,556 
Williams Scotsman International, Inc. 
 
 
6.88% due 08/15/236 
1,650,000 
1,733,605 
Sabre GLBL, Inc. 
 
 
5.38% due 04/15/236 
1,000,000 
1,025,000 
5.25% due 11/15/236 
625,000 
640,625 
Exide Technologies 
 
 
11.00% due 10/31/24†††,8,17 
2,591,725 
1,661,975 
LBC Tank Terminals Holding Netherlands BV 
 
 
6.88% due 05/15/236 
1,575,000 
1,587,474 
JB Poindexter & Company, Inc. 
 
 
7.13% due 04/15/266 
1,100,000 
1,147,300 
Exide International Holdings, LP 
 
 
10.75% (in-kind rate was 4.50%) due 10/31/21†††,8,16 
744,491 
710,989 
Party City Holdings, Inc. 
 
 
6.63% due 08/01/266 
875,000 
525,000 
Reliance Intermediate Holdings, LP 
 
 
6.50% due 04/01/236 
400,000 
412,000 
Total Consumer, Cyclical 
 
11,854,895 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 35


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
CORPORATE BONDS†† – 17.2% (continued) 
 
 
Consumer, Non-cyclical – 1.7% 
 
 
Nathan’s Famous, Inc. 
 
 
6.63% due 11/01/256 
2,050,000 
$ 2,070,500 
Nielsen Finance LLC / Nielsen Finance Co. 
 
 
5.00% due 04/15/226 
1,650,000 
1,660,313 
Sotheby’s 
 
 
7.38% due 10/15/276 
1,700,000 
1,659,625 
Vector Group Ltd. 
 
 
6.13% due 02/01/256 
1,725,000 
1,649,531 
Flexi-Van Leasing, Inc. 
 
 
10.00% due 02/15/236 
1,133,000 
1,079,182 
Acadia Healthcare Company, Inc. 
 
 
5.63% due 02/15/23 
600,000 
611,250 
KeHE Distributors LLC / KeHE Finance Corp. 
 
 
8.63% due 10/15/266 
550,000 
572,000 
Endo Finance LLC / Endo Finco, Inc. 
 
 
7.25% due 01/15/226 
800,000 
560,000 
Midas Intermediate Holdco II LLC / Midas Intermediate Holdco II Finance, Inc. 
 
 
7.88% due 10/01/226 
600,000 
513,000 
Avanos Medical, Inc. 
 
 
6.25% due 10/15/22 
500,000 
509,375 
Beverages & More, Inc. 
 
 
11.50% due 06/15/228 
650,000 
409,500 
Endo Dac / Endo Finance LLC / Endo Finco, Inc. 
 
 
6.00% due 07/15/236 
200,000 
130,000 
Carriage Services, Inc. 
 
 
6.63% due 06/01/266 
100,000 
104,750 
Total Consumer, Non-cyclical 
 
11,529,026 
 
Basic Materials – 1.2% 
 
 
BHP Billiton Finance USA Ltd. 
 
 
6.75% due 10/19/754,6 
2,450,000 
2,870,298 
Yamana Gold, Inc. 
 
 
4.95% due 07/15/24 
2,560,000 
2,683,122 
Neon Holdings, Inc. 
 
 
10.13% due 04/01/266 
1,625,000 
1,637,187 
Kaiser Aluminum Corp. 
 
 
5.88% due 05/15/24 
1,100,000 
1,144,000 
Mirabela Nickel Ltd. 
 
 
due 06/24/198,11 
1,388,176 
69,409 
Total Basic Materials 
 
8,404,016 
 
Communications – 1.0% 
 
 
Cengage Learning, Inc. 
 
 
9.50% due 06/15/246 
1,851,000 
1,567,186 
 
See notes to financial statements.

36 l GOF l GUGGENHIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
CORPORATE BONDS†† – 17.2% (continued) 
 
 
Communications – 1.0% (continued) 
 
 
Altice France S.A. 
 
 
7.38% due 05/01/266 
1,060,000 
$ 1,131,550 
McGraw-Hill Global Education Holdings LLC / McGraw-Hill Global Education Finance 
 
 
7.88% due 05/15/246 
1,346,000 
1,117,180 
EIG Investors Corp. 
 
 
10.88% due 02/01/24 
863,000 
847,898 
MDC Partners, Inc. 
 
 
6.50% due 05/01/246 
905,000 
823,550 
Houghton Mifflin Harcourt Publishers, Inc. 
 
 
9.00% due 02/15/256 
700,000 
668,640 
LCPR Senior Secured Financing DAC 
 
 
6.75% due 10/15/276 
500,000 
515,625 
Total Communications 
 
6,671,629 
 
Utilities – 0.4% 
 
 
Terraform Global Operating LLC 
 
 
6.13% due 03/01/266 
1,630,000 
1,695,200 
Petershill II Senior Secured Notes 
 
 
5.00% due 12/02/39††† 
1,000,000 
989,749 
Total Utilities 
 
2,684,949 
 
Technology – 0.0% 
 
 
NCR Corp. 
 
 
6.38% due 12/15/23 
200,000 
204,830 
Total Corporate Bonds 
 
 
(Cost $116,552,438) 
 
116,306,517 
 
COLLATERALIZED MORTGAGE OBLIGATIONS†† – 11.2% 
 
 
Residential Mortgage Backed Securities – 9.7% 
 
 
Lehman XS Trust Series 
 
 
2006-18N, 1.89% (1 Month USD LIBOR + 0.18%, Rate Floor: 0.18%) due 12/25/367 
4,871,814 
4,634,536 
2006-16N, 1.92% (1 Month USD LIBOR + 0.21%, Rate Floor: 0.21%) due 11/25/467 
1,957,870 
1,878,860 
WaMu Asset-Backed Certificates WaMu Series 
 
 
2007-HE4, 1.88% (1 Month USD LIBOR + 0.17%, Rate Floor: 0.17%) due 07/25/477 
2,254,461 
1,748,018 
2007-HE2, 1.96% (1 Month USD LIBOR + 0.25%, Rate Floor: 0.25%) due 04/25/377 
3,271,738 
1,714,636 
2007-HE2, 2.07% (1 Month USD LIBOR + 0.36%, Rate Floor: 0.36%) due 04/25/377 
2,093,912 
1,118,539 
2007-HE4, 1.96% (1 Month USD LIBOR + 0.25%, Rate Floor: 0.25%) due 07/25/477 
1,310,200 
912,600 
2007-HE2, 1.90% (1 Month USD LIBOR + 0.19%, Rate Floor: 0.19%) due 04/25/377 
1,701,304 
882,075 
LSTAR Securities Investment Limited 
 
 
2019-5, 3.20% (1 Month USD LIBOR + 1.50%, Rate Floor: 1.50%) due 11/01/246,7 
5,000,000 
4,991,685 
ACE Securities Corporation Home Equity Loan Trust Series 
 
 
2005-HE2, 2.73% (1 Month USD LIBOR + 1.02%, Rate Floor: 0.68%) due 04/25/357 
2,000,000 
2,006,227 
2007-HE1, 1.86% (1 Month USD LIBOR + 0.15%, Rate Floor: 0.15%) due 01/25/377 
2,909,577 
1,896,445 
2007-ASP1, 1.91% (1 Month USD LIBOR + 0.20%, Rate Floor: 0.20%) due 03/25/377 
1,574,512 
972,336 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 37


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
COLLATERALIZED MORTGAGE OBLIGATIONS†† – 11.2% (continued) 
 
 
Residential Mortgage Backed Securities – 9.7% (continued) 
 
 
Ameriquest Mortgage Securities Trust 
 
 
2006-M3, 1.88% (1 Month USD LIBOR + 0.18%, Rate Floor: 0.18%) due 10/25/367 
4,502,827 
$ 3,172,537 
2006-M3, 1.81% (1 Month USD LIBOR + 0.10%, Rate Floor: 0.10%) due 10/25/367 
2,262,838 
1,059,435 
GSAA Home Equity Trust 
 
 
2006-16, 1.88% (1 Month USD LIBOR + 0.17%, Rate Floor: 0.17%) due 10/25/367 
4,901,850 
2,189,233 
2006-12, 1.86% (1 Month USD LIBOR + 0.15%, Rate Floor: 0.15%) due 08/25/367 
3,408,160 
2,039,757 
Morgan Stanley ABS Capital I Incorporated Trust 
 
 
2006-HE8, 1.93% (1 Month USD LIBOR + 0.22%, Rate Floor: 0.22%) due 10/25/367 
3,462,695 
2,214,058 
2007-HE4, 1.94% (1 Month USD LIBOR + 0.23%, Rate Floor: 0.23%) due 02/25/377 
3,681,822 
1,678,037 
RALI Series Trust 
 
 
2006-QO6, 1.89% (1 Month USD LIBOR + 0.18%, Rate Floor: 0.18%) due 06/25/467 
6,609,247 
2,553,123 
2006-QO6, 1.94% (1 Month USD LIBOR + 0.23%, Rate Floor: 0.23%) due 06/25/467 
2,091,048 
832,947 
LSTAR Securities Investment Trust 
 
 
2019-1, 3.41% (1 Month USD LIBOR + 1.70%, Rate Floor: 0.00%) due 03/01/246,7 
3,238,497 
3,240,116 
Long Beach Mortgage Loan Trust 
 
 
2006-8, 1.80% (1 Month USD LIBOR + 0.09%, Rate Floor: 0.09%) due 09/25/367 
4,661,538 
1,858,096 
2006-1, 1.90% (1 Month USD LIBOR + 0.19%, Rate Floor: 0.19%) due 02/25/367 
1,400,905 
1,242,373 
Morgan Stanley IXIS Real Estate Capital Trust 
 
 
2006-2, 1.93% (1 Month USD LIBOR + 0.22%, Rate Floor: 0.22%) due 11/25/367 
3,208,716 
1,594,928 
2006-2, 1.86% (1 Month USD LIBOR + 0.15%, Rate Floor: 0.15%) due 11/25/367 
2,117,753 
1,042,110 
Home Equity Mortgage Loan Asset-Backed Trust Series INABS 
 
 
2006-E, 1.92% (1 Month USD LIBOR + 0.21%, Rate Floor: 0.21%) due 04/25/377 
3,274,630 
2,424,458 
American Home Mortgage Assets Trust 
 
 
2006-6, 1.92% (1 Month USD LIBOR + 0.21%, Rate Floor: 0.21%) due 12/25/467 
2,546,996 
2,213,003 
Citigroup Mortgage Loan Trust, Inc. 
 
 
2007-AMC3, 2.06% (1 Month USD LIBOR + 0.35%, Rate Floor: 0.35%) due 03/25/377 
2,382,793 
2,090,739 
JP Morgan Mortgage Acquisition Trust 
 
 
2006-WMC3, 1.95% (1 Month USD LIBOR + 0.24%, 
 
 
Rate Floor: 0.24%) due 08/25/367 
2,719,454 
2,047,230 
Master Asset Backed Securities Trust 
 
 
2006-WMC3, 1.87% (1 Month USD LIBOR + 0.16%, 
 
 
Rate Floor: 0.16%) due 08/25/367 
3,770,353 
1,760,108 
IXIS Real Estate Capital Trust 
 
 
2007-HE1, 1.82% (1 Month USD LIBOR + 0.11%, Rate Floor: 0.11%) due 05/25/377 
2,540,944 
862,023 
2007-HE1, 1.77% (1 Month USD LIBOR + 0.06%, Rate Floor: 0.06%) due 05/25/377 
2,555,858 
859,764 
Morgan Stanley Mortgage Loan Trust 
 
 
2006-9AR, 1.86% (1 Month USD LIBOR + 0.15%, Rate Floor: 0.15%) due 08/25/367 
3,703,334 
1,644,309 
First NLC Trust 
 
 
2007-1, 1.99% (1 Month USD LIBOR + 0.28%, Rate Floor: 0.28%) due 08/25/376,7 
1,532,072 
994,724 
GSAA Trust 
 
 
2007-3, 1.88% (1 Month USD LIBOR + 0.17%, Rate Floor: 0.17%) due 03/25/477 
1,824,370 
835,243 
Luminent Mortgage Trust 
 
 
2006-2, 1.91% (1 Month USD LIBOR + 0.20%, Rate Floor: 0.20%) due 02/25/467 
903,376 
797,911 
 
See notes to financial statements.

38 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
COLLATERALIZED MORTGAGE OBLIGATIONS†† – 11.2% (continued) 
 
 
Residential Mortgage Backed Securities – 9.7% (continued) 
 
 
CitiMortgage Alternative Loan Trust Series 
 
 
2007-A7, 2.11% (1 Month USD LIBOR + 0.40%, 
 
 
Rate Cap/Floor: 7.50%/0.40%) due 07/25/377 
969,017 
$ 784,428 
TBW Mortgage Backed Pass-Through Certificates 
 
 
2006-6, 6.04% due 01/25/3717 
1,185,071 
530,528 
2006-6, 5.75% due 01/25/3717 
484,704 
233,630 
Total Residential Mortgage Backed Securities 
 
65,550,805 
 
Military Housing – 1.5% 
 
 
GMAC Commercial Mortgage Asset Corp. 
 
 
2004-POKA, 6.36% due 09/10/44†††,6 
3,500,000 
4,166,888 
Freddie Mac Military Housing Bonds Resecuritization Trust Certificates 
 
 
2015-R1, 5.49% (WAC) due 11/25/527,8 
3,708,110 
3,652,260 
Capmark Military Housing Trust 
 
 
2007-AETC, 5.75% due 02/10/526,17 
1,587,677 
1,775,245 
2007-AET2, 6.06% due 10/10/526,17 
474,961 
574,922 
Total Military Housing 
 
10,169,315 
Total Collateralized Mortgage Obligations 
 
 
(Cost $79,306,102) 
 
75,720,120 
 
FOREIGN GOVERNMENT DEBT†† – 6.4% 
 
 
Government of Japan 
 
 
due 01/10/2012 
JPY 1,112,000,000 
10,165,810 
0.10% due 06/01/20 
JPY 439,400,000 
4,021,297 
0.10% due 09/01/20 
JPY 407,000,000 
3,727,346 
0.10% due 06/20/20 
JPY 166,000,000 
1,519,455 
0.10% due 04/15/20 
JPY 142,900,000 
1,307,399 
0.10% due 03/20/20 
JPY 58,000,000 
530,533 
2.40% due 03/20/20 
JPY 24,000,000 
221,014 
1.30% due 03/20/20 
JPY 10,000,000 
91,793 
2.20% due 06/22/20 
JPY 6,650,000 
61,574 
Federative Republic of Brazil 
 
 
due 01/01/2012 
BRL 25,900,000 
6,102,246 
due 07/01/2112 
BRL 19,940,000 
4,366,030 
due 07/01/2012 
BRL 9,860,000 
2,274,420 
State of Israel 
 
 
1.00% due 04/30/21 
ILS 20,810,000 
6,067,638 
5.50% due 01/31/22 
ILS 5,410,000 
1,736,518 
0.50% due 01/31/21 
ILS 4,520,000 
1,307,426 
Total Foreign Government Debt 
 
 
(Cost $44,342,782) 
 
43,500,499 
 
MUNICIPAL BONDS†† – 0.2% 
 
 
Maryland – 0.1% 
 
 
Maryland Economic Development Corp. 
 
 
5.75% due 09/01/25 
550,000 
564,195 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 39


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
MUNICIPAL BONDS†† – 0.2% (continued) 
 
 
Oklahoma – 0.1% 
 
 
Oklahoma Development Finance Authority Revenue Bonds 
 
 
5.45% due 08/15/28 
400,000 
$ 455,272 
Total Municipal Bonds 
 
 
(Cost $964,554) 
 
1,019,467 
 
SENIOR FIXED RATE INTERESTS†† – 0.1% 
 
 
Communications – 0.1% 
 
 
MHGE Parent LLC 
 
 
11.00% due 04/20/22†††,1 
900,000 
826,987 
Total Senior Fixed Rate Interests 
 
 
(Cost $886,514) 
 
826,987 
 
U.S. TREASURY BILLS†† – 0.1% 
 
 
U.S. Treasury Bills 
 
 
1.59% due 02/20/2013,17 
400,000 
398,616 
Total U.S. Treasury Bills 
 
 
(Cost $398,570) 
 
398,616 
 
REPURCHASE AGREEMENTS††,14 – 0.4% 
 
 
Citigroup Global Markets, Inc. 
 
 
issued 10/16/19 at 1.35% 
 
 
open maturity15 
1,016,000 
1,016,000 
issued 10/08/19 at 1.35% 
 
 
open maturity15 
436,000 
436,000 
issued 10/25/19 at 1.25% 
 
 
open maturity15 
93,000 
93,000 
issued 11/25/19 at 1.35% 
 
 
open maturity15 
83,000 
83,000 
issued 10/30/19 at 1.30% 
 
 
open maturity15 
51,000 
51,000 
BofA Securities, Inc. 
 
 
issued 10/09/19 at 1.40% 
 
 
open maturity15 
448,950 
448,950 
issued 10/16/19 at 1.35% 
 
 
open maturity15 
328,575 
328,575 
issued 10/25/19 at 1.35% 
 
 
open maturity15 
93,288 
93,287 
issued 08/02/19 at 1.40% 
 
 
open maturity15 
59,850 
59,850 
RBC Capital Markets LLC 
 
 
issued 11/01/19 at 1.30% 
 
 
open maturity15 
52,375 
52,375 
 
See notes to financial statements.

40 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 
 

 
 
Face 
 
 
Amount~ 
Value 
 
REPURCHASE AGREEMENTS††,14 – 0.4% (continued) 
 
 
BNP Paribas 
 
 
issued 02/06/19 at 1.35% 
 
 
open maturity15 
4,638 
$ 4,638 
Total Repurchase Agreements 
 
 
(Cost $2,666,675) 
 
2,666,675 
 
COMMERCIAL PAPER†† – 0.3% 
 
 
Bemis Co., Inc. 
 
 
1.88% due 12/12/196,13 
2,000,000 
1,998,851 
Total Commercial Paper 
 
 
(Cost $1,998,851) 
 
1,998,851 

     
 
Notional Value/ 
 
 
Face Amount~ 
 
 
OTC OPTIONS PURCHASED†† – 0.2% 
 
 
Put options on: 
 
 
Citibank N.A., New York 2Y-10 CMS CAP 
 
 
Expiring July 2022 with strike price of $0.40 
441,000,000 
$ 679,140 
Bank of America, N.A. 2Y-10 CMS CAP 
 
 
Expiring July 2022 with strike price of $0.61 
165,000,000 
161,700 
Bank of America, N.A. 2Y-10 CMS CAP 
 
 
Expiring July 2022 with strike price of $0.40 
53,000,000 
81,620 
Total OTC Options Purchased 
 
 
(Cost $1,391,950) 
 
922,460 
Total Investments – 100.8% 
 
 
(Cost $707,218,725) 
 
$ 680,973,057 
 
Corporate Bonds Sold Short†† – (0.4)% 
 
 
Communications – 0.0% 
 
 
Univision Communications, Inc. 
 
 
5.13% due 05/15/236 
(50,000) 
(49,312) 
5.13% due 02/15/256 
(150,000) 
(144,563) 
Total Communications 
 
(193,875) 
 
Industrial – (0.2)% 
 
 
Flex Ltd. 
 
 
4.75% due 06/15/25 
(170,000) 
(183,035) 
Spirit AeroSystems, Inc. 
 
 
4.60% due 06/15/28 
(810,000) 
(878,492) 
Total Industrial 
 
(1,061,527) 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 41


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2019 
 

 
 
Face 
 
 
Amount~ 
Value 
 
Corporate Bonds Sold Short†† – (0.4)% (continued) 
 
 
Consumer, Cyclical – (0.2)% 
 
 
Harley-Davidson, Inc. 
 
 
3.50% due 07/28/25 
(100,000) 
$ (104,154) 
Dollar Tree, Inc. 
 
 
4.00% due 05/15/25 
(1,200,000) 
(1,266,246) 
Total Consumer, Cyclical 
 
(1,370,400) 
Total Corporate Bonds Sold Short 
 
 
(Proceeds $2,369,340) 
 
(2,625,802) 

     
 
Contracts 
 
 
LISTED OPTIONS WRITTEN– 0.0% 
 
 
Call options on: 
 
 
S&P 500 Index 
 
 
Expiring December 2019 with strike price of 
 
 
$3,105.00 (Notional Value $942,294) 
(17,355) 
Total Listed Options Written 
 
 
(Premiums received $12,834) 
 
(17,355) 
Other Assets & Liabilities, net – (0.4)% 
 
(2,534,398) 
Total Net Assets – 100.0% 
 
$ 675,795,502 
 
FUTURES CONTRACTS
         
 
 
 
 
Value and 
 
Number of 
 
Notional 
Unrealized 
Description 
Contracts 
Expiration Date 
Amount 
Appreciation** 
 
EQUITY FUTURES CONTRACTS PURCHASED 
 
 
 
 
S&P 500 Index Mini Futures Contracts 
Dec 2019 
$942,600 
$40,208 
 
CENTRALLY CLEARED CREDIT DEFAULT SWAP AGREEMENTS PROTECTION PURCHASED††
                   
 
 

Protection
 
 
 
 
Upfront 
 
 
 
 
Premium 
Payment 
Maturity 
Notional 
 
Premiums 
Unrealized 
Counterparty 
Exchange 
Index 
Rate 
Frequency 
Date 
Amount 
Value 
Received 
Depreciation** 
BofA Securities, Inc. 
ICE 
CDX.NA.IG.31 
1.00% 
Quarterly 
12/20/23 
$98,500,000 
$(2,405,693) 
$(944,702) 
$(1,460,991) 
 
See notes to financial statements.

42 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2019 
 
OTC CREDIT DEFAULT SWAP AGREEMENTS PROTECTION PURCHASED††
                 
 
 
 
 
 
 
 
Upfront 
 
 
Index/ 
Protection
 
 
 
 
Premiums 
 
 
Reference 
Premium
Payment 
Maturity 
Notional 
 
Paid 
Unrealized 
Counterparty 
Obligation 
Rate 
Frequency 
Date 
Amount 
Value 
(Received) 
Depreciation**
Goldman Sachs 
 
 
 
 
 
 
 
 
International 
L Brands, Inc. 
1.00% 
Quarterly 
12/20/24 
$ 30,000 
$ 2,550 
$ 3,179 
$ (629) 
Morgan Stanley 
CDX.NA.IG.31 
 
 
 
 
 
 
 
Capital Services LLC 
(7-15%) 
1.00% 
Quarterly 
12/20/23 
5,800,000 
(144,441) 
(1,118) 
(143,323) 
Goldman Sachs 
CDX.NA.IG.31 
 
 
 
 
 
 
 
International 
(7-15%) 
1.00% 
Quarterly 
12/20/23 
13,410,000 
(333,958) 
(17,793) 
(316,165) 
 
 
 
 
 
 
$(475,849) 
$(15,732) 
$(460,117) 
 
CENTRALLY CLEARED INTEREST RATE SWAP AGREEMENTS††
                   
 
 
Floating 
Floating 
Fixed Payment 
Maturity 
Notional 
 
Premiums 
Unrealized 
Counterparty 
Exchange 
Rate Type
Rate Index 
Rate Frequency 
Date 
Amount 
Value 
Paid 
Appreciation** 
BofA Securities, Inc. 
CME
Receive 
3-Month 
1.54% Quarterly 
08/04/21 
$2,390,000 
$4,891 
$263 
$4,628 
 
 
 
USD LIBOR 
 
 
 
 
 
 
 
TOTAL RETURN SWAP AGREEMENTS
               
 
 
Financing 
 
 
 
 
Value and 
 
Reference 
Rate 
Payment 
Maturity 
 
Notional 
Unrealized 
Counterparty 
Obligation 
Pay 
Frequency 
Date 
Units 
Amount 
Depreciation** 
OTC Sovereign Debt Swap Agreements††
 
 
 
 
Deutsche 
Korea 
 
 
 
 
 
 
Bank AG 
Monetary 
 
 
 
 
 
 
 
Stabilization 
2.34% (3 Month 
At Maturity 
08/04/21 
N/A 
$2,418,367 
$(15,683) 
 
Bond 
USD LIBOR + 0.45%) 
 
 
 
 
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 43


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2019 
 

   
FORWARD FOREIGN CURRENCY EXCHANGE CONTRACTS††
 
 
     
 
 
       
Value at
   
Unrealized
 
 
     
   
Settlement 
 
Settlement
   
November 30,
   
Appreciation
 
Counterparty 
 
Contracts to Sell
 
Currency 
Date 
 
Value
   
2019
   
(Depreciation)
 
Goldman Sachs International 
   
1,777,600,000
 
JPY 
01/10/20 
 
$
16,579,924
   
$
16,301,156
   
$
278,768
 
Citibank N.A., New York 
   
25,900,000
 
BRL 
01/02/20 
   
6,314,237
     
6,121,485
     
192,752
 
Citibank N.A., New York 
   
11,240,000
 
BRL 
07/01/21 
   
2,716,438
     
2,559,645
     
156,793
 
Goldman Sachs International 
   
5,420,000
 
BRL 
07/01/20 
   
1,407,427
     
1,271,395
     
136,032
 
Barclays Bank plc 
   
2,366,000
 
EUR 
01/17/20 
   
2,732,494
     
2,616,303
     
116,191
 
Goldman Sachs International 
   
2,290,000
 
EUR 
01/17/20 
   
2,644,305
     
2,532,262
     
112,043
 
Citibank N.A., New York 
   
4,440,000
 
BRL 
07/01/20 
   
1,143,623
     
1,041,512
     
102,111
 
JPMorgan Chase Bank, N.A. 
   
407,203,500
 
JPY 
09/01/20 
   
3,870,646
     
3,784,385
     
86,261
 
Citibank N.A., New York 
   
379,189,500
 
JPY 
06/01/20 
   
3,587,277
     
3,505,830
     
81,447
 
Citibank N.A., New York 
   
444,400,000
 
JPY 
01/10/20 
   
4,143,474
     
4,075,289
     
68,185
 
Goldman Sachs International 
   
5,700,000
 
BRL 
07/01/21 
   
1,335,364
     
1,298,040
     
37,324
 
Bank of America, N.A. 
   
166,083,000
 
JPY 
06/22/20 
   
1,570,822
     
1,537,355
     
33,467
 
Bank of America, N.A. 
   
142,971,450
 
JPY 
04/15/20 
   
1,348,545
     
1,318,179
     
30,366
 
JPMorgan Chase Bank, N.A. 
   
3,000,000
 
BRL 
07/01/21 
   
712,674
     
683,179
     
29,495
 
Bank of America, N.A. 
   
749,320
 
EUR 
06/15/20 
   
861,699
     
836,372
     
25,327
 
Goldman Sachs International 
   
660,240
 
EUR 
06/15/20 
   
759,659
     
736,943
     
22,716
 
JPMorgan Chase Bank, N.A. 
   
58,029,000
 
JPY 
03/23/20 
   
548,032
     
534,289
     
13,743
 
JPMorgan Chase Bank, N.A. 
   
60,430,200
 
JPY 
06/01/20 
   
571,147
     
558,713
     
12,434
 
Goldman Sachs International 
   
260,000
 
EUR 
04/30/20 
   
298,168
     
289,380
     
8,788
 
Goldman Sachs International 
   
34,353,000
 
JPY 
03/23/20 
   
324,553
     
316,297
     
8,256
 
Goldman Sachs International 
   
6,723,951
 
JPY 
06/22/20 
   
63,635
     
62,241
     
1,394
 
JPMorgan Chase Bank, N.A. 
   
203,500
 
JPY 
03/02/20 
   
1,912
     
1,871
     
41
 
Citibank N.A., New York 
   
189,500
 
JPY 
12/02/19 
   
1,770
     
1,732
     
38
 
Bank of America, N.A. 
   
43,318
 
ILS 
04/30/20 
   
12,646
     
12,609
     
37
 
Bank of America, N.A. 
   
83,000
 
JPY 
12/20/19 
   
775
     
760
     
15
 
Goldman Sachs International 
   
73,150
 
JPY 
12/20/19 
   
684
     
670
     
14
 
JPMorgan Chase Bank, N.A. 
   
30,200
 
JPY 
12/02/19 
   
282
     
276
     
6
 
Deutsche Bank AG 
   
7,680,324
 
KRW 
02/04/21 
   
6,512
     
6,582
     
(70
)
Deutsche Bank AG 
   
7,680,324
 
KRW 
11/04/20 
   
6,492
     
6,562
     
(70
)
Deutsche Bank AG 
   
7,429,879
 
KRW 
05/06/21 
   
6,315
     
6,386
     
(71
)
Deutsche Bank AG 
   
7,680,324
 
KRW 
08/05/20 
   
6,473
     
6,546
     
(73
)
Deutsche Bank AG 
   
7,513,360
 
KRW 
05/06/20 
   
6,310
     
6,387
     
(77
)
Deutsche Bank AG 
   
7,680,324
 
KRW 
02/05/20 
   
6,430
     
6,515
     
(85
)
Goldman Sachs International 
   
165,352
 
ILS 
04/30/20 
   
47,654
     
48,132
     
(478
)
Bank of America, N.A. 
   
1,009,000
 
EUR 
12/13/19 
   
1,112,303
     
1,112,782
     
(479
)
Goldman Sachs International 
   
320,150
 
ILS 
01/31/20 
   
91,758
     
92,590
     
(832
)
Bank of America, N.A. 
   
4,363,200
 
ILS 
04/30/21 
   
1,293,950
     
1,296,950
     
(3,000
)
Goldman Sachs International 
   
1,135,000
 
GBP 
12/13/19 
   
1,457,914
     
1,468,523
     
(10,609
)
Goldman Sachs International 
   
4,841,027
 
ILS 
02/01/21 
   
1,410,169
     
1,432,227
     
(22,058
)
Deutsche Bank AG 
   
2,876,875,324
 
KRW 
08/04/21 
   
2,453,415
     
2,479,892
     
(26,477
)
Goldman Sachs International 
   
5,707,550
 
ILS 
01/31/22 
   
1,691,893
     
1,719,844
     
(27,951
)
Barclays Bank plc 
   
8,085,000
 
ILS 
01/31/20 
   
2,287,452
     
2,338,258
     
(50,806
)
Goldman Sachs International 
   
16,654,900
 
ILS 
04/30/21 
   
4,882,148
     
4,950,625
     
(68,477
)
 
       
 
 
                 
$
1,342,431
 
 
See notes to financial statements.

44 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2019 
 

   
FORWARD FOREIGN CURRENCY EXCHANGE CONTRACTS†† (continued)
 
 
     
 
 
       
Value at
   
Unrealized
 
 
     
   
Settlement 
 
Settlement
   
November 30,
   
Appreciation
 
Counterparty 
 
Contracts to Buy
 
Currency 
Date 
 
Value
   
2019
   
(Depreciation)
 
Citibank N.A., New York 
   
8,085,000
 
ILS 
01/31/20 
 
$
2,317,966
   
$
2,338,258
   
$
20,292
 
Citibank N.A., New York 
   
260,000
 
EUR 
04/30/20 
   
290,382
     
289,380
     
(1,002
)
Barclays Bank plc 
   
1,409,560
 
EUR 
06/15/20 
   
1,578,236
     
1,573,315
     
(4,921
)
JPMorgan Chase Bank, N.A. 
   
4,656,000
 
EUR 
01/17/20 
   
5,176,715
     
5,148,566
     
(28,149
)
JPMorgan Chase Bank, N.A. 
   
1,110,000,000
 
JPY 
01/10/20 
   
10,266,380
     
10,179,052
     
(87,328
)
 
       
 
 
                 
$
(101,108
)
 
 
The face amount is denominated in U.S. dollars unless otherwise indicated. 
Non-income producing security. 
** 
Includes cumulative appreciation (depreciation). Variation margin is reported within the Statement of Assets and Liabilities. 
† 
Value determined based on Level 1 inputs, unless otherwise noted — See Note 6. 
†† 
Value determined based on Level 2 inputs, unless otherwise noted — See Note 6. 
††† 
Value determined based on Level 3 inputs — See Note 6. 
Security was fair valued by the Valuation Committee at November 30, 2019. The total market value of fair valued securities amounts to $26,962,273, (cost $27,399,619) or 4.0% of total net assets. 
Affiliated issuer. 
Perpetual maturity. 
Security has a fixed rate coupon which will convert to a floating or variable rate coupon on a future date. 
Rate indicated is the 7-day yield as of November 30, 2019. 
Security is a 144A or Section 4(a)(2) security. These securities have been determined to be liquid under guidelines established by the Board of Trustees. The total market value of 144A or Section 4(a)(2) securities is $160,686,705 (cost $160,641,972), or 23.8% of total net assets. 
Variable rate security. Rate indicated is the rate effective at November 30, 2019. In some instances, the effective rate is limited by a minimum rate floor or a maximum rate cap established by the issuer. The settlement status of a position may also impact the effective rate indicated. In some cases, a position may be unsettled at period end and may not have a stated effective rate. In instances where multiple underlying reference rates and spread amounts are shown, the effective rate is based on a weighted average. 
Security is a 144A or Section 4(a)(2) security. These securities have been determined to be illiquid and restricted under guidelines established by the Board of Trustees. The total market value of 144A or Section 4(a)(2) illiquid and restricted securities is $27,620,536 (cost $44,816,083), or 4.1% of total net assets — See Note 12. 
Security has no stated coupon. However, it is expected to receive residual cash flow payments on defined deal dates. 
10 
Security is a step up bond, with a 5.50% coupon rate until September 14, 2020. Future rate is 8.50% with a reset date of September 15, 2020. 
11 
Security is in default of interest and/or principal obligations. 
12 
Zero coupon rate security. 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 45


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2019 
 
 
 
13 
Rate indicated is the effective yield at the time of purchase. 
14 
Repurchase Agreements - See additional disclosure in the repurchase agreements table below for more information on repurchase agreements. 
15 
The rate is adjusted periodically by the counterparty, subject to approval by the Adviser, and is not based upon a set reference rate and spread. Rate indicated is the rate effective at November 30, 2019. 
16 
Payment in-kind security. 
17 
All or a portion of these securities have been physically segregated in connection with futures contracts, options and unfunded loan commitments. As of November 30, 2019, the total value of segregated securities was $15,136,851. 
 
   
BofA 
Bank of America 
BRL 
Brazilian Real 
CDX.NA.IG.31 
Credit Default Swap North American Investment Grade Series 31 Index 
CME 
Chicago Mercantile Exchange 
CMS 
Constant Maturity Swap 
EURIBOR 
European Interbank Offered Rate 
EUR 
Euro 
GBP 
British Pound 
ICE 
Intercontinental Exchange 
ILS 
Israeli New Shekel 
JPY 
Japanese Yen 
KRW 
South Korean Won 
LIBOR 
London Interbank Offered Rate 
plc 
Public Limited Company 
WAC 
Weighted Average Coupon 
 
See Sector Classification in Other Information section.
     
Country Diversification
 
 
% of Long-Term 
Country 
 
Investments 
United States 
 
84.9% 
Cayman Islands 
 
4.7% 
Japan 
 
3.4% 
Brazil 
 
2.0% 
Canada 
 
1.6% 
Israel 
 
1.4% 
Australia 
 
0.9% 
Other 
 
1.1% 
Total Long-Term Investments 
 
100.0% 
 
See notes to financial statements.

46 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2019 
 
The following table summarizes the inputs used to value the Fund’s investments at November 30, 2019 (See Note 6 in the Notes to Financial Statements):
                         
 
       
Level 2
   
Level 3
       
 
       
Significant
   
Significant
       
Investments in 
 
Level 1
   
Observable
   
Unobservable
       
Securities (Assets) 
 
Quoted Prices
   
Inputs
   
Inputs
   
Total
 
Common Stocks 
 
$
130,448
   
$
1,444,843
   
$
699,488
   
$
2,274,779
 
Preferred Stocks 
   
     
2,244,182
     
591,396
     
2,835,578
 
Warrants 
   
     
     
131
     
131
 
Closed-End Funds 
   
29,090,842
     
     
     
29,090,842
 
Money Market Fund 
   
9,049,257
     
     
     
9,049,257
 
Senior Floating Rate Interests 
   
     
209,778,896
     
66,904,383
     
276,683,279
 
Asset-Backed Securities 
   
     
104,902,983
     
12,776,016
     
117,678,999
 
Corporate Bonds 
   
     
95,682,713
     
20,623,804
     
116,306,517
 
Collateralized Mortgage Obligations 
   
     
71,553,232
     
4,166,888
     
75,720,120
 
Foreign Government Debt 
   
     
43,500,499
     
     
43,500,499
 
Municipal Bonds 
   
     
1,019,467
     
     
1,019,467
 
Senior Fixed Rate Interests 
   
     
     
826,987
     
826,987
 
U.S. Treasury Bills 
   
     
398,616
     
     
398,616
 
Repurchase Agreements 
   
     
2,666,675
     
     
2,666,675
 
Commercial Paper 
   
     
1,998,851
     
     
1,998,851
 
Options Purchased 
   
     
922,460
     
     
922,460
 
Equity Futures Contracts* 
   
40,208
     
     
     
40,208
 
Interest Rate Swap Agreements* 
   
     
4,628
     
     
4,628
 
Forward Foreign Currency Exchange Contracts* 
   
     
1,574,336
     
     
1,574,336
 
Total Assets 
 
$
38,310,755
   
$
537,692,381
   
$
106,589,093
   
$
682,592,229
 

   
 
         
Level 2
   
Level 3
         
 
         
Significant
   
Significant
         
Investments in 
 
Level 1
   
Observable
   
Unobservable
         
Securities (Liabilities) 
 
Quoted Prices
   
Inputs
   
Inputs
   
Total
 
Corporate Bonds Sold Short 
 
$
   
$
2,625,802
   
$
   
$
2,625,802
 
Options Written 
   
17,355