Runako Morton was left to fight a lone battle as Leeward Islands crashed to an innings-and 55-run defeat to Barbados on the third day in Philipsburg. The Leewards captain made an enterprising 102 off 144 balls - his 11th first-class century - striking 14 fours and two sixes, as another insipid batting display followed from the first innings. Leewards started the day on 66 for 1, requiring 303 to avoid an innings defeat, and looked set to force the match into the final day. They proceeded to 131 for 3 at lunch, after play started an hour late because of rain. The largest partnership of the innings was a 64-run fourth-wicket effort between Morton and Omari Banks (19) but Leewards lost their last six wickets for a mere 46 runs, with the Barbados attack putting the innings into a tailspin. Ryan Hinds, voted Man of the Match for his outstanding 240 in Barbados' first innings, picked up 3 for 29 with Pedro Collins, Tino Best and Kemar Roach bagging two wickets each.
Trinidad & Tobago displayed their all-round dominance to stay on course for victory against the Windward Islands in Trinidad. The hosts were bolstered by fifties from captain Daren Ganga, Lendl Simmons and Denesh Ramdin, after bowling out Windwards for 181 in the morning session. The visitors avoided the follow-on when the last pair of Deighton Butler and Mervyn Matthew held on for almost an hour to go past the critical mark of 161. With a handsome first-innings lead, T&T set about positioning themselves for their first win in the tournament as Simmons and Ganga went on the offensive, scoring heavily in the post-lunch session. The declaration on 243 for 5 came soon after Denesh Ramdin's half-century and the T&T spinners tightened the noose on Windwards, leaving them on 82 for 3, still needing 291 for the win.
A penetrative opening spell from Andrew Richardson handed the advantage back to Jamaica after they were bowled out for a modest 165 in their second innings against the Combined Campuses & Colleges (CCC) in Barbados. Richardson picked up 3 for 13 and CCC, set 221 for victory, reached 103 for 5 at stumps. Resuming on 32 for 1, Donovan Pagon (44) and Brenton Parchment (42) put on 69 for the second wicket for Jamaica, but the rest of the batsmen failed to cross 18. The defending champions and current table-toppers were all out about half-an-hour before the rescheduled tea break. Khismar Catlin and Ryan Austin were the most successful bowlers for CCC with three wickets apiece. During the chase, Richardson removed Romel Currency, Nekoli Parris and captain Simon Jackson as CCC crashed to 16 for 3. Floyd Reifer (35) and Chadwick Walton (30) steadied the innings before they were dismissed in the final hour.