In 2019 the Sharks posted the best regular-season record in the league and won a best-of-three series against the Newport Gulls to win the Southern Division, but ultimately lost 2–0 in the NECBL Championship to the Keene Swamp Bats.

[citation needed] The team's home games are played at Vineyard Baseball Park, located on the Martha's Vineyard Regional High School campus in Oak Bluffs, Massachusetts, where $200,000 has been invested in field upgrades and construction of a field house, public restrooms, and a pro-style backstop with netting and brick facade.

The Sharks were in first place for a majority of the season, before injuries and a team-wide viral illness caused them to fall behind.

The Sharks moved to the NECBL in 2019 and posted the league's best regular-season record in their first season, including a 12-game win streak.

In 2022, they went 5–0 in the playoffs to win their first NECBL league championship, and also hosted the 2022 all-star game with attendance exceeding 5,000 fans.