Johann Myburgh scored 88 off 58 balls to lead Hampshire to a competitive total against Windward Islands, after which Hamza Riazuddin's four-wicket spell helped secure a narrow victory, and with it a spot in the Caribbean T20 final. Hampshire had a solid start to their innings, with Jimmy Adams and Myburgh adding 47 in 6 overs before Adams was run out. Myburgh provided the acceleration, striking six sixes during his half-century, while James Vince made 36 off 32 balls. Myburgh, who was eventually bowled by Mervin Matthew with the score on 160, was the only batsman dismissed by a Windward bowler. The other three wickets in the score of 166 for 4 were run out.
Windward lost Johnson Charles early but Andre Fletcher and Devon Smith steadied the chase. They didn't score at breakneck speed but they led Windward to 75 in the 10th over, when Riazuddin struck for the first time, getting Smith caught behind. Keddy Lesporis was run out for 6 but Windward were still in it, at 114 for 3, when the 16th over began. In that over, Riazuddin ripped out three wickets, reducing the innings to 116 for 6, and severely broke Windward's momentum. Riazuddin finished with 4 for 15, and even though Matthew blasted 27 off 15, Windward fell four runs short.
Trinidad & Tobago's passage to the final was easier as they beat Jamaica by eight wickets with 13 balls to spare in the second semi-final. The result ensured T&T's qualification to the Champions League later this year by virtue of being the best Caribbean side in the competition.
Jamaica's innings failed to take off as wickets fell regularly and the run-rate struggled to rise over six. The top four batsmen fell for less than 20 and strike-rates of less than 100. Wavell Hinds and Andre Russell provided some stability, scoring 23 and 36, but the tail folded after their departures. T&T legspinner Samuel Badree, who opened the bowling, finished with 1 for 15 in four overs, while Ravi Rampaul and Sunil Narine picked up two wickets each. T&T needed only 137 to set up a summit clash with Hampshire.
The top order did the job, with Adrian Barath making 37 and Lendl Simmons contributing 51. Darren Bravo continued his impressive form, scoring 25 off 19 balls at No. 3, to lead T&T to 140 for 2 in the 18th over. Of the six bowlers Jamaica used, only Jerome Taylor took a wicket.