Trinidad and Tobago made it six wins out of six, beating Barbados by 41 runs in Port of Spain. After choosing to bat, they were in trouble at 5 for 3 but captain Denesh Ramdin and Jason Mohammed put together a match-winning stand. Ramdin struck 134 at better than a run a ball, with 12 fours and four sixes, and Mohammed played a steady hand of 63. The pair added 170 and helped take the score to 264 for 8. Seamer Marlon Richards struck early for T&T in the chase and he was supported by the rest of the bowling contingent, as Barbados lost wickets at frequent intervals. Though many of their batsmen got starts, only one, Jonathan Carter, went on to score a half-century. Shannon Gabriel, Rayad Emrit, and Yannick Cariah bagged two wickets each, as Barbados were bowled out for 223.
Leeward Islands slipped to their fifth defeat, losing to Windward Islands by 36 runs in a low-scoring game in Antigua. Windwards chose to bat and though Leewards struck regularly, the middle order, led by a half-century from captain Liam Sebastien, took their team to 194 for 9. Jacques Taylor took four wickets but his effort was in vain. Six of Leewards' batsmen reached double-figures but no one stuck around long enough to guide the chase. Shane Shillingford, who had an excellent home Test series against Zimbabwe, grabbed his best returns in List A cricket, taking 6 for 32, and restricting Leewards to just 158 for 9.
Jamaica will meet Windward Islands in the semi-final after they beat Guyana by two wickets in a rain-affected match in Guyana. Electing to bat, Guyana could not put up a challenging score as David Bernard (4 for 24) and Nkrumah Bonner (3 for 23) struck regularly. Guuyana then lost four wickets within 15 runs and managed to score 190 for 9 in 49 overs, as Anthony Bramble and Assad Fudadin top-scored with 31 each. Jamaica's top five batsmen put together only 55 runs but Carlton Baugh's 40 and double-digit scores from Nikita Miller and Andrew Richardson for the ninth wicket completed the chase off the last ball.