Windward Islands held off a determined effort from West Indies Under-19s on the opening day of Group A matches to win by 21 runs in North Sound. Sunil Ambris added 70 for the fourth wicket with captain Liam Sebastien and top-scored with 54 off 84 balls in Windwards' total of 221. Keemo Paul burrowed through the middle order before wrapping up the tail, taking the last wicket two balls into the 47th over to finish with figures of 4 for 31 for West Indies Under-19s.

In reply, Bhaskar Yadram scored 52 at No. 3 for the junior side but got little support as West Indies Under-19s struggled to string a decent partnership together. There were only two 40-plus partnerships in the innings: 45 runs between Yadram and Shamar Springer for the fourth wicket, and 40 runs between Paul and Kirstan Kallicharan for the sixth wicket. Paul and Kallicharan were part of six batsmen down the order who reached double-figures but couldn't make it past 25 as extras wound up the next best contributor behind Yadram with 32 runs. Mervin Matthew dismantled the lower order to finish with 4 for 38, claiming Man-of-the-Match honours as West Indies Under-19s finished on 200 for 9.

In the late game at Coolidge, Leeward Islands defeated Kent by seven wickets, chasing a target of 229 with 6.3 overs to spare. Nkrumah Bonner steered the successful chase by scoring an unbeaten 78. Fast bowler Gavin Tonge had been the biggest obstacle in the Kent innings, taking 4 for 39 to restrict the English county side to 233, with their top score coming from Calum Haggett, who scored 45 off 59 balls at No. 7. Kent's score was revised to 228 after umpires imposed a five-run penalty.