The team competes in regional cricket under the franchise name Leeward Islands Hurricanes.

The list of prominent cricketers who have played for the Leewards Islands includes Curtly Ambrose, Eldine Baptiste, Kenny Benjamin, Winston Benjamin, Sheldon Cottrell, George Ferris, Ridley Jacobs, Viv Richards, Richie Richardson, Andy Roberts and Hayden Walsh Jr.

The Leeward Islands played their inaugural first-class game in 1958, and lost by an innings and 19 runs to Jamaica.

Their first win did not come until 1968–69, when they beat Guyana by 43 runs at the Warner Park Sporting Complex ground.

The Leeward Islands have also played home games at Salem Oval (Montserrat), Edgar Gilbert Sporting Complex (Saint Kitts), Carib Lumber Ball Park (Sint Maarten), Addelita Cancryn Junior High School Ground (St. Thomas) and Elquemedo Willet Park (Nevis).