UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _________ to _________ Commission File Number: 001-34042 MAIDEN HOLDINGS, LTD. (Exact Name of Registrant As Specified in Its Charter) Bermuda 98-0570192 (State or Oth ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 (State or other jurisdiction of incorporation or organization) 94 Pitts Bay Road Pembroke (Address of principal executive offices) (Zip Code) Bermuda 98-0570192 (IRS Employer Identificatio ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _________ to _________ Commission File No. 001-34042 MAIDEN HOLDINGS, LTD. (Exact name of registrant as specified in its charter) Bermuda 98-0570192 (State or oth ...

PART I - Financial Information [Financial Statements](index=3&type=section&id=Item%201.%20Financial%20Statements) Maiden Holdings reported a **$20.9 million** net income in Q1 2020, reversing a **$36.6 million** net loss from the prior year, driven by lower underwriting losses and realized investment gains Condensed Consolidated Statements of Income Highlights (Q1 2020 vs Q1 2019) | Metric | Q1 2020 (in thousands) | Q1 2019 (in thousands) | | :--- | :--- | :--- | | Net Premiums Earned | $31,215 | $183,102 | | Total Revenues | $59,119 | $204,835 | | Total Expenses | $38,243 | $238,775 | | **Net Income (Loss)** | **$20,861** | **$(36,636)** | | Basic and Diluted EPS | $0.25 | $(0.44) | Condensed Consolidated Balance Sheet Highlights (as of March 31, 2020) | Metric | March 31, 2020 (in thousands) | December 31, 2019 (in thousands) | | :--- | :--- | :--- | | Total Investments | $1,542,632 | $1,867,266 | | Total Assets | $3,321,757 | $3,568,196 | | Total Liabilities | $2,836,759 | $3,060,478 | | **Total Shareholders' Equity** | **$484,998** | **$507,718** | Condensed Consolidated Statements of Cash Flows Highlights (Q1 2020 vs Q1 2019) | Metric | Q1 2020 (in thousands) | Q1 2019 (in thousands) | | :--- | :--- | :--- | | Net Cash Used in Operating Activities | $(218,481) | $(331,930) | | Net Cash Provided by Investing Activities | $288,530 | $129,781 | | Net Increase (Decrease) in Cash | $70,684 | $(202,483) | [Notes to Condensed Consolidated Financial Statements](index=8&type=section&id=Notes%20to%20Condensed%20Consolidated%20Financial%20Statements) Notes detail strategic changes, including cessation of active reinsurance underwriting, re-domestication, and AmTrust run-off, impacting investments and key agreements - The company has ceased active reinsurance underwriting and is focused on running off its existing liabilities, with a key strategic move being the re-domestication of Maiden Reinsurance from Bermuda to Vermont effective March 16, 2020, to better align capital with its U.S.-based liabilities[23](index=23&type=chunk)[28](index=28&type=chunk) - The company's reportable segments are Diversified Reinsurance (primarily European property and casualty business) and AmTrust Reinsurance (all business ceded from AmTrust, now in run-off)[29](index=29&type=chunk)[41](index=41&type=chunk) - The LPT/ADC Agreement with Enstar's affiliate, Cavello, provides **$155 million** in adverse development cover over the carried AmTrust Quota Share loss reserves as of December 31, 2018, resulting in a deferred gain liability of **$113.0 million** as of March 31, 2020[95](index=95&type=chunk)[94](index=94&type=chunk) - The company recognized net favorable prior year loss development of **$0.5 million** in Q1 2020, compared to adverse development of **$7.3 million** in Q1 2019, driven by no development in the AmTrust Reinsurance segment in 2020 versus **$8.1 million** of adverse development in 2019[99](index=99&type=chunk)[100](index=100&type=chunk)[101](index=101&type=chunk) [Management's Discussion and Analysis of Financial Condition and Results of Operations](index=33&type=section&id=Item%202.%20Management's%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management confirms the company is in reinsurance run-off, focusing on asset and capital management, with lower premiums and negative operating cash flow - The company is not actively underwriting reinsurance and is running off liabilities from terminated AmTrust contracts, with a strategic focus shifted to asset and capital management to generate shareholder returns[144](index=144&type=chunk)[146](index=146&type=chunk) - The COVID-19 pandemic has adversely impacted the company's investment portfolio, causing significant unrealized losses (**$44.2 million** in Q1 2020) due to widening credit spreads, also heightening liquidity risk and potentially requiring additional capital or collateral posting[154](index=154&type=chunk)[244](index=244&type=chunk)[245](index=245&type=chunk) Key Financial Metrics (Q1 2020 vs Q1 2019) | Metric | Q1 2020 | Q1 2019 | | :--- | :--- | :--- | | Net Income (Loss) | $20.9 million | $(36.6) million | | Combined Ratio | 131.6% | 129.9% | | Non-GAAP Operating Earnings (Loss) | $3.1 million | $(27.6) million | | Book Value per Common Share | $0.24 | N/A (vs $0.51 at YE 2019) | - The company expects continued significant negative operating cash flow (**$218.5 million** in Q1 2020) due to the run-off of its reinsurance liabilities, with these outflows expected to be funded by cash, investment income, and proceeds from investment sales[233](index=233&type=chunk)[234](index=234&type=chunk)[236](index=236&type=chunk) [Controls and Procedures](index=56&type=section&id=Item%204.%20Controls%20and%20Procedures) Management, including CEO and CFO, concluded disclosure controls were effective as of March 31, 2020, with no material changes to internal controls - The Chief Executive Officer and Chief Financial Officer concluded that the company's disclosure controls and procedures were effective as of the end of the period covered by the report[283](index=283&type=chunk) - No changes in the company's internal controls over financial reporting occurred during the most recent fiscal quarter that have materially affected, or are reasonably likely to materially affect, these controls[284](index=284&type=chunk) PART II - Other Information [Legal Proceedings](index=57&type=section&id=Item%201.%20Legal%20Proceedings) The company refers to Note 11 for legal matters and reports no material changes from previously disclosed legal proceedings - The company is subject to a putative class action complaint filed in February 2019, alleging violations of the Exchange Act related to inadequate loss reserves in connection with reinsurance provided to AmTrust, which the company believes is without merit and intends to defend vigorously[133](index=133&type=chunk) [Risk Factors](index=57&type=section&id=Item%201A.%20Risk%20Factors) The COVID-19 pandemic significantly impacts the company's business, financial condition, and liquidity, posing risks to investments, financing, and operations - The COVID-19 pandemic is identified as a significant risk factor that has adversely impacted, and is expected to continue to adversely impact, the company's business, financial condition, and liquidity[288](index=288&type=chunk)[289](index=289&type=chunk) - Specific COVID-19 related risks include continued unrealized losses and volatility in the investment portfolio, potential negative impacts on the ability to raise additional capital, reduced liquidity from increased collateral requirements, and operational disruptions due to remote work[289](index=289&type=chunk)[290](index=290&type=chunk)[291](index=291&type=chunk) [Unregistered Sales of Equity Securities and Use of Proceeds](index=58&type=section&id=Item%202.%20Unregistered%20Sales%20of%20Equity%20Securities%20and%20Use%20of%20Proceeds) The company has a remaining authorization of **$74.2 million** for share repurchases as of March 31, 2020, with no repurchases in Q1 2020 - The company has a remaining authorization of **$74,245,000** for share repurchases as of March 31, 2020[295](index=295&type=chunk) - No share repurchases were made under the authorized plan during the three months ended March 31, 2020[295](index=295&type=chunk) [Exhibits](index=59&type=section&id=Item%206.%20Exhibits) This section lists Form 10-Q exhibits, including an amended termination endorsement and required CEO and CFO certifications - Key exhibits filed include an Amended Termination Endorsement between Maiden Reinsurance Ltd. and AmTrust subsidiaries, as well as required CEO and CFO certifications[299](index=299&type=chunk)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2019 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _________ to _________ Commission File Number: 001-34042 MAIDEN HOLDINGS, LTD. (Exact Name of Registrant As Specified in Its Charter) Bermuda 98-0570192 (State or Other Jurisdic ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Commission File No. 001-34042 MAIDEN HOLDINGS, LTD. (Exact name of registrant as specified in its charter) (State or other jurisdiction of incorporation or organization) 94 Pitts Bay Road Pembroke FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Fo ...

PART I - Financial Information [Item 1. Financial Statements](index=3&type=section&id=Item%201.%20Financial%20Statements) The financial statements for H1 2019 reflect a company in significant transition, with total assets decreasing and a net loss of $52.0 million [Condensed Consolidated Balance Sheets](index=3&type=section&id=Condensed%20Consolidated%20Balance%20Sheets) Balance Sheet Summary (as of June 30, 2019 vs. Dec 31, 2018) | Metric | June 30, 2019 ($ thousands) | Dec 31, 2018 ($ thousands) | Change (%) | | :--- | :--- | :--- | :--- | | Total Investments | 3,000,029 | 4,090,965 | (26.7)% | | Total Assets | 4,598,556 | 5,287,460 | (13.0)% | | Total Liabilities | 4,007,984 | 4,732,544 | (15.3)% | | Total Equity | 590,572 | 554,916 | 6.4% | - The significant decrease in total assets and liabilities is primarily due to the strategic restructuring, including the termination of the AmTrust Quota Share agreement, which led to a large reduction in unearned premiums and related assets[10](index=10&type=chunk)[101](index=101&type=chunk) - Total equity increased despite a net loss, driven by a significant positive swing in Accumulated Other Comprehensive Income from **$(65.6) million** to **$21.2 million**, reflecting unrealized gains on the investment portfolio[10](index=10&type=chunk) [Condensed Consolidated Statements of Income](index=4&type=section&id=Condensed%20Consolidated%20Statements%20of%20Income) Income Statement Highlights (Six Months Ended June 30) | Metric | 2019 ($ thousands) | 2018 ($ thousands) | Change (%) | | :--- | :--- | :--- | :--- | | Net Premiums Earned | 317,088 | 1,021,201 | (68.9)% | | Total Revenues | 394,721 | 1,094,032 | (63.9)% | | Net (Loss) Income from Continuing Operations | (29,999) | 6,813 | N/A | | (Loss) Income from Discontinued Operations | (22,050) | 18,210 | N/A | | Net (Loss) Income | (52,049) | 25,023 | N/A | | Basic & Diluted (Loss) Earnings Per Share | $(0.63) | $0.09 | N/A | - The dramatic drop in Net Premiums Earned is a direct result of the termination of the AmTrust Quota Share and the sale of the U.S. treaty reinsurance operations[12](index=12&type=chunk)[26](index=26&type=chunk)[101](index=101&type=chunk) - The company swung to a significant net loss, driven by both a loss from continuing operations and a substantial loss from discontinued operations related to the sale of its U.S. business[12](index=12&type=chunk)[92](index=92&type=chunk) [Condensed Consolidated Statements of Cash Flows](index=7&type=section&id=Condensed%20Consolidated%20Statements%20of%20Cash%20Flows) Cash Flow Summary (Six Months Ended June 30) | Activity | 2019 ($ thousands) | 2018 ($ thousands) | | :--- | :--- | :--- | | Net Cash (Used in) Provided by Operating Activities | (503,657) | 56,104 | | Net Cash Provided by Investing Activities | 630,908 | 22,200 | | Net Cash Used in Financing Activities | (13) | (42,208) | - Operating cash flow turned sharply negative, primarily due to a **$459.2 million** decrease in unearned premiums related to the termination of the AmTrust Quota Share[17](index=17&type=chunk)[101](index=101&type=chunk) - Investing activities provided significant cash inflow of **$630.9 million**, driven by proceeds from sales of fixed-maturity securities exceeding purchases, likely to fund operational needs and strategic transactions[17](index=17&type=chunk) [Notes to Condensed Consolidated Financial Statements](index=8&type=section&id=Notes%20to%20Condensed%20Consolidated%20Financial%20Statements) Notes detail significant corporate actions including U.S. operations sale, AmTrust Quota Share termination, and de-risking transactions - As part of a strategic review, the company sold its U.S. treaty reinsurance operations (Maiden US) to Enstar and terminated its significant quota share agreements with AmTrust[24](index=24&type=chunk)[26](index=26&type=chunk) - The company and its subsidiary Maiden Bermuda failed to meet their Enhanced Capital Requirement (ECR) as of **Dec 31, 2018**, prompting a series of remediation measures[23](index=23&type=chunk) - Subsequent to quarter-end, on **July 31, 2019**, the company entered into a Loss Portfolio Transfer and Adverse Development Cover (LPT/ADC) agreement with Enstar to assume liabilities from the AmTrust Quota Share in excess of a **$2.18 billion** retention[133](index=133&type=chunk) - Also on **July 31, 2019**, the company entered into a Commutation and Release Agreement with AmTrust to assume all reserves for specific California and New York workers' compensation business in exchange for a payment of **$312.8 million**[140](index=140&type=chunk)[141](index=141&type=chunk) [Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations](index=39&type=section&id=Item%202.%20Management%27s%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management discusses the company's transformation, including U.S. operations sale and AmTrust contract termination [Results of Operations](index=46&type=section&id=Results%20of%20Operations) For Q2 2019, the company reported a net loss of $15.4 million, driven by discontinued operations and higher underwriting loss Consolidated Performance (Three Months Ended June 30) | Metric | 2019 | 2018 | | :--- | :--- | :--- | | Net (Loss) Attributable to Common Shareholders | $(15,413) thousand | $(5,913) thousand | | Underwriting Loss | $(39,131) thousand | $(32,035) thousand | | Net Loss and LAE Ratio | 90.2% | 73.1% | | Expense Ratio | 46.4% | 35.0% | | Combined Ratio | 136.6% | 108.1% | - The higher net loss in Q2 2019 was primarily driven by a **$18.7 million** loss from discontinued operations and an increased underwriting loss, which was impacted by adverse prior year loss development of **$26.0 million**[177](index=177&type=chunk)[178](index=178&type=chunk) [Underwriting Results by Reportable Segment](index=51&type=section&id=Underwriting%20Results%20by%20Reportable%20Segment) Diversified Reinsurance improved profitability, while AmTrust Reinsurance, now in run-off, reported a substantial underwriting loss Diversified Reinsurance Segment - Q2 Performance | Metric | 2019 | 2018 | | :--- | :--- | :--- | | Underwriting Income (Loss) | $490 thousand | $(174) thousand | | Net Premiums Written | $8,718 thousand | $29,717 thousand | | Combined Ratio | 97.9% | 100.6% | AmTrust Reinsurance Segment - Q2 Performance | Metric | 2019 | 2018 | | :--- | :--- | :--- | | Underwriting Loss | $(39,645) thousand | $(31,861) thousand | | Net Premiums Written | $(9,127) thousand | $491,311 thousand | | Combined Ratio | 135.5% | 106.7% | [Liquidity and Capital Resources](index=56&type=section&id=Liquidity%20and%20Capital%20Resources) Liquidity was strained with negative operating cash flow, but post-quarter transactions improved capital ratios - The company experienced negative operating cash flow of **$503.7 million** in H1 2019, compared to positive **$56.1 million** in H1 2018, due to the termination of the AmTrust Quota Share[236](index=236&type=chunk)[237](index=237&type=chunk) - As a result of remediation measures, including the LPT/ADC Agreement with Enstar and the Commutation with AmTrust, the Company and Maiden Bermuda met and exceeded their respective ECR ratios as of **July 31, 2019**[230](index=230&type=chunk) - The company has voluntarily undertaken with the Bermuda Monetary Authority (BMA) not to make any capital distributions, including common or preference share dividends, without the BMA's express consent[231](index=231&type=chunk) - The duration of the investment portfolio (**3.1 years**) was shorter than the duration of loss reserves (**3.9 years**) as of **June 30, 2019**, a gap expected to narrow following the LPT and commutation agreements[249](index=249&type=chunk) [Item 3. Quantitative and Qualitative Disclosures About Market Risk](index=60&type=page&id=Item%203.%20Quantitative%20and%20Qualitative%20Disclosures%20About%20Market%20Risk) Primary market risks include interest rate, credit, and foreign exchange, with significant exposure to interest rate fluctuations Interest Rate Sensitivity Analysis (as of June 30, 2019) | Hypothetical Change in Interest Rates | Estimated Change in Fair Value ($ thousands) | Hypothetical % (Decrease) Increase in Shareholders' Equity | | :--- | :--- | :--- | | 100 basis point increase | (117,992) | (20.0)% | | 100 basis point decrease | 110,066 | 18.6% | - The company's fixed maturity investment portfolio is high quality, with **99.1%** of securities rated investment grade as of **June 30, 2019**[253](index=253&type=chunk)[275](index=275&type=chunk) - Significant counterparty credit risk exists with AmTrust related to funds withheld receivables totaling over **$633 million** and a **$168 million** loan[274](index=274&type=chunk)[279](index=279&type=chunk) [Item 4. Controls and Procedures](index=61&type=page&id=Item%204.%20Controls%20and%20Procedures) Management concluded disclosure controls were effective as of June 30, 2019, with no material changes to internal controls - The CEO and CFO concluded that as of the end of the reporting period, the company's disclosure controls and procedures were effective[284](index=284&type=chunk) - No changes in internal controls over financial reporting that have materially affected, or are reasonably likely to materially affect, the company's internal control over financial reporting occurred during the quarter[285](index=285&type=chunk) PART II - Other Information [Item 1. Legal Proceedings](index=62&type=page&id=Item%201.%20Legal%20Proceedings) The company is involved in routine legal proceedings, including a putative class action complaint alleging misrepresentations - A putative class action complaint was filed against Maiden Holdings and certain officers on **February 11, 2019**, alleging violations of the Exchange Act by making misrepresentations about the company's business, risk management, and underwriting policies[125](index=125&type=chunk) [Item 1A. Risk Factors](index=62&type=page&id=Item%201A.%20Risk%20Factors) No material changes from the risk factors disclosed in the 2018 Form 10-K were reported - No material changes from the risk factors disclosed in the 2018 Form 10-K were reported[288](index=288&type=chunk) [Item 2. Unregistered Sales of Equity Securities and Use of Proceeds](index=62&type=page&id=Item%202.%20Unregistered%20Sales%20of%20Equity%20Securities%20and%20Use%20of%20Proceeds) The company has a share repurchase program with $74.2 million remaining authorization, but no shares were repurchased in Q2 2019 - No shares were repurchased under the company's publicly announced share repurchase plan in the three months ended **June 30, 2019** The remaining authorization is **$74.2 million**[290](index=290&type=chunk)[291](index=291&type=chunk)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _________ to _________ Commission File No. 001-34042 MAIDEN HOLDINGS, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdi ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2018 OR Commission File Number: 001-34042 MAIDEN HOLDINGS, LTD. (Exact Name of Registrant As Specified in Its Charter) (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer Identification No.) Bermuda 98-0570192 94 Pitts Bay Road Pembroke HM 08, Bermuda (Address of Principal Exec ...