Guyana 164 for 5 (Johnson 30) beat Leeward Islands 162 (Hamilton 40, Barnwell 4-31, Bishoo 3-35) by five wickets
Scorecard

Guyana started their Regional Super50 campaign on a winning note as they chased Leeward Islands' total of 162, to win by five wickets. Leeward Islands' innings could not gather any momentum as legspinner Devendra Bishoo and fast medium bowler Christopher Barnwell claimed wickets regularly, taking three and four respectively.

Guyana's reply started solidly with Rajindra Chandrika scoring 28 before being run out. At one stage Guyana were struggling at 90 for 4, but Assad Fudadin and wicketkeeper Derwin Christian took them home with almost six overs to spare.

Jamaica 239 for 8 (Bonner 110, Miller 42*) beat Barbados 164 (Lambert 3-22) by 75 runs
Scorecard

A century from Nkrumah Bonner and a combined bowling effort, led by offspinner Tamar Lambert, helped Jamaica clinch a commanding 75-run victory over Barbados in the Regional Super50 tie at Kensington Oval. Although Jamaica lost wickets regularly after choosing to bat, Bonner's 110 helped them reach 239. In reply, four of Barbados batsmen got starts, but no one scored more than 28, and this hurt them as they were bowled out for 164. Spinners Lambert and Nikita Miller, and seamer Sheldon Cotterell did most of the damage, sharing seven wickets between them.

Jamaica lead the points table due to the big margin of the win, which helped them jump over Guyana and Windward Islands, both of whom won their respective games.

Windward Islands 211 for 9 (Fletcher 67, Smith 54, Dewar 3-23) beat Combined Campuses and Colleges 207 (Reifer 60, Walton 56, Shillingford 4-39) by one wicket
Scorecard

Windward Islands overhauled Combined Campuses and Colleges' target of 207, to claim a one-wicket victory, thanks largely to fifties from Andre Fletcher and Devon Smith. Shane Shillingford's spell of 4 for 39 proved decisive as CCC could not put together an effective partnership. Raymon Reifer struck 60 before being run out, with wicketkeeper Chadwick Wilson being the only other player to pass 50.

Devon Smith and Andre Fletcher led the way for Windwards in their reply with scores of 54 and 67. Despite their dismissal, Windwards seemed on course for victory, but a mini-collapse later on placed them at a precarious 186 for 9. Tailenders Delorn Johnson and Nelon Pascal, however, held their nerve and ensured their team started the tournament with a win.