Windward Islands sealed their fourth straight win in the Caribbean T20, edging past Guyana in a closely-fought, rain-affected game at the Kensington Oval in Barbados. Choosing to field, Guyana, relying on important contributions from opener Sewnarine Chattergoon (27) and captain Christopher Barnwell (32) and a late surge from Veerasammy Permaul, reached 140 for 8 in 20 overs. Darren Sammy picked up 3 for 11, excellent figures in a four-over spell. All of his wickets came in one over.

Rain intervened after Windwards had reached 5 without loss in the chase, and the target was revised to 119 in 16 overs and Windwards just about managed that. Opener Johnson Charles led the way with 65, off 43 balls, striking three fours and three sixes. Charles was the third wicket to fall with the score on 88, and Windwards needed 31 off 21 balls at the time.

Though Devendra Bishoo bowled economically, picking three for 15 in four overs, Devon Smith saw Windwards through, making an unbeaten 25 off 19 balls with two fours and a six. In the final over, at the fall of Shane Shillingford's wicket, Windwards needed 3 off 3 balls and the win was sealed off the last ball of the match. Windwards are among the two decided semi-finalists.

In another rain-affected match at the same venue, Trinidad and Tobago brushed aside Canada, winning by eight wickets and sealing their place in the semi-finals. Canada, after opting to bat, began in encouraging fashion, their openers Hiral Patel and Ruvindu Gunasekera adding 43 for the first wicket. But the innings fell apart after that, nine wickets falling for 56 runs. No one else, apart from the extras column, reached double-figures and Canada were kept to 99 for 9. Ravi Rampaul was the wrecker-in-chief, taking 4 for 26, and Dwayne Bravo helped him out with 3 for 20 in four overs.

T&T lost Lendl Simmons early and Adrian Barath was given out obstructing the field upon deviating the wicketkeeper's throw. Darren Bravo and Denesh Ramdin, however, ensured there were no further hiccups. Rain halted play in the 12th over and the target was revised to 91 in 18 overs. Darren Bravo top-scored with an unbeaten 42 off 41 balls and Ramdin chipped in with 30 off 27 in a 59-run stand. The win was achieved in the 16th over.