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☑ ☐ 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 , 2020 OR TRANSITION REPORT PURSUANT TO SECTION 13 OR 15 ( d ) OF THE SECURITIES EXCHANGE ACT OF 1934 to For the transition period from Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP , LTD . ( Exact name of Registrant as specified in its charter ) Bermuda ( State or other jurisdiction of incorporation or organization ) 23 South Main Street , Suite 3B Hanover , New Hampshire ( Address of principal executive offices ) Title of each class 94-2708455 ( I.R.S. Employer Identification No. ) 03755-2053 ( Zip Code ) Registrant's telephone number , including area code : ( 603 ) 640-2200 Securities registered pursuant to Section 12 ( b ) of the Act : Common Shares , par value $ 1.00 per share Trading Symbol ( s ) WTM Name of each exchange on which registered New York Stock Exchange Bermuda Stock Exchange Securities registered pursuant to Section 12 ( g ) of the Act : None Indicate by check mark if the Registrant is a well - known seasoned issuer , as defined in Rule 405 of the Securities Act . Yes ý No o Indicate by check mark if the Registrant is not required to file reports pursuant to Section 13 or Section 15 ( d ) of the Act . Yes o No ý Indicate by check mark whether the Registrant ( 1 ) has filed all reports required to be filed by Section 13 or 15 ( d ) of the Securities Exchange Act of 1934 during the preceding 12 months ( or for such shorter period that the registrant was required to file such reports ) , and ( 2 ) has been subject to such filing requirements for the past 90 days . Yes ý No o Indicate by check mark whether the Registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S - T ( $ 232.405 of this chapter ) during the preceding 12 months ( or for such shorter period that the Registrant was required to submit such files ) . Yes ý No o Indicate by check mark whether the Registrant is a large accelerated filer , an accelerated filer , a non - accelerated filer , a smaller reporting company , or an emerging growth company . See definitions of " large accelerated filer , " " accelerated filer , " " smaller reporting company , " and " emerging growth company ” in Rule 12b - 2 of the Exchange Act . Large accelerated filer ý Accelerated filer o Smaller reporting company ☐ Emerging growth company ☐ Non - accelerated filer If an emerging growth company , indicate by check mark if the Registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13 ( a ) of the Exchange Act . O Indicate by check mark whether the registrant has filed a report on and attestation to its management's assessment of the effectiveness of its internal control over financial reporting under Section 404 ( b ) of the Sarbanes - Oxley Act ( 15 U.S.C. 7262 ( b ) ) by the registered public accounting firm that prepared or issued its audit report . ý Indicate by check mark whether the Registrant is a shell company ( as defined in Rule 12b - 2 of the Act ) . Yes □ No ý The aggregate market value of voting shares ( based on the closing price of those shares listed on the New York Stock Exchange and the consideration received for those shares not listed on a national or regional exchange ) held by non - affiliates of the Registrant as of June 30 , 2020 , was $ 2,685,847,299 . As of February 24 , 2021 , 3,095,829 common shares , par value of $ 1.00 per share , were outstanding ( which includes 28,405 restricted common shares that were not vested at such date ) . DOCUMENTS INCORPORATED BY REFERENCE Portions of the Registrant's Definitive Proxy Statement to be filed with the Securities and Exchange Commission ( " SEC " ) pursuant to Regulation 14A under the Securities Exchange Act of 1934 , as amended ( the " Exchange Act " ) , relating to the Registrant's Annual General Meeting of Members scheduled to be held May 27 , 2021 are incorporated by reference into Part III of this Form 10 - K . With the exception of the portions of the Proxy Statement specifically incorporated herein by reference , the Proxy Statement is not deemed to be filed as part of this Form 10 - K .