5 March - Former Cabinet Minister Mark Vanterpool abruptly resigns from politics just eight days after winning his seat in the 2019 general election.[6]
14 March - Former Cabinet Minister Mark Vanterpool withdraws his resignation and alleges it was legally invalid.[7] A dispute arises with the Speaker of the House as to whether the seat is vacant or not.
April
24 April - Controversy arises in relation to a non-tender US$98,000 six month consultancy contract awarded by the new Government to Claude Skelton-Cline, a media personality who endorsed the party. Contracts under US$100,000 are not required to be tendered under local law.[8]
Mark Vanterpool is successful in his court action validating his claim to still be entitled to take up his seat in the House of Assembly despite attempting to resign before being sworn in.[10]
Controversy arises in relation to a non-tendered purchase of a $115,000 vehicle for the use of the premier.[11]
August
28 August - The Territory is struck lightly by Hurricane Dorian. No deaths or serious injuries are reported.
September
5 September - The exemption from requiring a work permit in favour of students is repealed.[12]
13 September - Phase 1 of the new territorial system for addresses is rolled out.[13]
†Physiographically, these continental islands are not part of the volcanic Windward Islands arc, although sometimes grouped with them culturally and politically.
#Bermuda is an isolated North Atlanticoceanic island, physiographically not part of the Lucayan Archipelago, Antilles, Caribbean Sea nor North American continental nor South American continental islands. It is grouped with the Northern American region, but occasionally also with the Caribbean region culturally.
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