The earliest match recorded in Bermuda took place on August 30, 1844, when the local garrison lost to another army team, although since the island was colonized in 1701, it seems more than likely that the game was played there in the 18th century. In 1855 Bermuda Cricket Club was formed, and it not surprising the the first visitors came from the nearby USA when Philadelphia Zingari visited in March 1891, playing the first international matches there, and the first Bermuda touring team, Hamilton Cricket Club, played in New York and Philadelphia in 1905.

The 1912 Australians popped in on their way home, but the cricketing strength of the island fell away after World War One, tours of poor quality sides taking place. The only tour of significance in the inter-War period being that of Sir Julien Cahn's team in 1933 - the five matches they played being the subject of much discussion for several years afterwards.

After the Second World War, enthusiasm for cricket gained ground and improvements in traveling led to more tours, particularly by West Indian sides, while Bermuda themselves visited England in 1960.

Bermuda became an Associate member of the ICC in 1966 and it was their delegate, Alma Hunt, who first proposed that a competition be held among the Associate members. This proposal led to the first ICC Trophy in England in 1979. In the second ICC Trophy in 1982, Bermuda advanced to the final without losing a match, but subsequent competitions have not seen this high standard kept up.

Bermuda remained on the periphery until they qualified for the 2007 World Cup courtesy of a fourth-place finish in the 2005 ICC Trophy. An US$11 million investment from the government plus extra income from Alan Stanford's competition gave the locals real hope that the country could breach the gap between Associates and Full Members.

The highlight of the domestic season is the annual Cup Match, played between two of the island's leading clubs - Somerset and St. George's. The match was first played in 1902 and the event is a public holiday, largely because so many locals took the time off anyway, and has taken on a carnival atmosphere.

Alma Hunt was, perhaps, the best cricketer produced by the island - he had some success in a trial match in Trinidad in 1933 prior to the selection of the West Indian side to tour England the following season, but doubts were raised about his eligibility - in the end he was not chosen. He was later an outstanding professional with Aberdeenshire and played for Scotland.