Leeward Islands made a steady beginning in their fifth-round match against Windward Islands at Bourda, reaching 254 for 5. They were led by Monticin Hodge's half-century and steady contributions by Kieran Powell and Gavin Williams. Openers Hodge and Mali Richards started slowly, before Richards tried to flick Shane Shillingford down the leg side and gave a catch to the wicketkeeper. He didn't look too pleased with the umpire's verdict, though. Powell walked in and batted briskly as Leewards went to lunch at 63 for 1. Powell continued batting aggressively in the afternoon session but fell two short of his fifty when he holed out to long-on. Hodge, who played the supporting role till then, reached his fifty off 165 balls. He and Williams took the score to 161 for 2 at tea. However, Windwards hit back to take two wickets for six runs, including Hodge for 61 and Williams for 44. Steven Liburd and Omari Banks mixed aggression with defence to take the score to 229 before Liburd failed to pick a fuller delivery from Shillingford, trapped lbw offering no shot.
A five-wicket haul by offspinner Ryan Austin saw Jamaica collapse under lights against Combined Campuses and Colleges at the Guyana National Stadium. Jamaica were well placed at 151 for 1, but wasted the start provided by Danza Hyatt and Donavan Pagon to collapse to 191 for 9. Pagon and Hyatt made good use of a placid pitch and brought up their half-centuries midway through the post-lunch session. Both hit six fours in getting to their respective milestones. But Austin struck in the final over before tea, trapping Hyatt lbw with a quicker delivery. Pagon fell for 80 when he edged to the keeper down the leg side off left-arm spinner Kavesh Kantasingh. Austin then had Nkrumah Bonner trapped lbw and then had Tamar Lambert caught at short leg. David Bernard was then caught at silly point and Austin picked up his fifth wicket when Bevan Brown holed out to deep midwicket. Kantasingh took 3 for 44 as CCC claimed the final session and the day's honours.
Half-centuries by Ryan Hinds, Jason Haynes and Dale Richards put Barbados in a commanding position at 326 for 5 against Guyana at the Albion Sports Complex. Hinds hit 13 fours and a six in his 76 and shared a stand of 126 for the third wicket with Haynes, who hit 69. Richards dominated an opening stand of 76 with Kraigg Braithwaite and hit eight fours. But he fell to a great catch by Brandon Bess running backwards at long-on. Hinds fell to a soft dismissal when he steered Royston Crandon to gully. Guyana then picked up two more wickets after Hinds' dismissal. Christopher Barnwell took two wickets while Zaheer Mohammed, Bess and Devendra Bishoo took a wicket each.