The Leeward Islands played their inaugural first-class game in 1958, and lost by an innings and 19 runs to Jamaica. However, their first win did not come until 1968–69, when they beat Guyana by 43 runs at the Warner Park Sporting Complex ground. From 1965–66 to 1980–81 the team competed as the Combined Islands in first-class cricket, along with the best cricketers from the Windward Islands. However, when regular one-day competitions began in 1975–76 the island groups were separate, and the Leeward Islands won on their third outing in 1977–78.