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. 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.
In 1981–82 the Leeward Islands made their debut in the Shell Shield with a 57-run win over the Windward Islands (the season after the Combined Islands had won the title), but it was to take eight seasons until they could lift the first-class trophy – which by then had been renamed the Red Stripe Cup. From 1989–90 to 1997–98, the Leeward Islands won three outright first-class titles with one shared and three outright one-day titles with one shared. Since then their only major trophy has been their 2010–11 WICB Cup triumph.
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Rakheem Cornwall (First-class) [1] 
Jahmar Hamilton (List A)
Warner Park 
Elquemedo Willett Park 
Salem Oval 
Carib Lumber Ball Park 
Addelita Cancryn 
