Windward Islands beat Jamaica by 17 runs at the Kensington Oval in Bridgetown, but both teams went through to the semi-finals since Jamaica still had a better net run-rate than Guyana and Somerset. Windwards completed their third win after electing to bat and scoring 165, a total that proved a few too many to chase for Jamaica. Windwards' openers got them off to a brisk start, and then Devon Smith and Keddy Lesporis got half-centuries in quick time. Smith remained unbeaten on 58 off 39 balls. Seamer Krishmar Santokie took three wickets for Jamaica while David Bernard was their most economical bowler, giving away just 20 runs in his four overs.

Jamaica lost a couple of early wickets in their chase, and left-arm spinner Gary Mathurin, who was used as an opening bowler by Windwards, stifled their innings, as he bowled a miserly spell of four overs for just nine runs with one wicket. Marlon Samuels and Wavell Hinds resurrected Jamaica's innings, both getting half-centuries, but they couldn't score fast enough and ended up falling well short of the target.

In the first match, Somerset had comfortably beaten Combined Campuses and Colleges. Somerest chose to bat, reached 165 and then restricted CCC to 123 in a dominant performance. Nick Compton and James Hildreth did the bulk of the scoring for Somerset, putting together a 90-run partnership for the second wicket. Hildreth stayed unbeaten on 69, and Craig Meschede played a cameo at the end, hammering 26 off 11 balls.

CCC were never in the chase, as they lost wickets at regular intervals. Seamer Steve Kirby did the early damage for Somerset, and finished with figures of 3 for 26, and then left-arm spinner George Dockrell put the choke on in the middle overs, taking 2 for 15 in his four overs.