If Lendl Simmons' fluent hundred on day-night one gave Trinidad & Tobago a running start, Denesh Ramdin's unbeaten ton on the second helped them extend the early advantage against Guyana at the Vivian Richards Stadium. Ramdin and Dave Mohammed frustrated the Guyana attack with a productive association for the eighth wicket worth 85. Mohammed contributed 37 before falling to Esuan Crandon. Narsingh Deonarine brought an end to proceedings with a couple of lbw dismissals that were separated by a 28-run stand for the last wicket that gave Ramdin his sixth first-class hundred and took T&T past 400. Ramdin's efforts were cautious to begin with, but he opened up in style as the day progressed. He spanked the new pink cherry, taken after 119 overs, for two fours through the covers and later reached his ton with a similar shot. Rayad Emrit put Guyana's reply in early strife by prising out Sewnarine Chattergoon before Rajindra Chandrika led the reply with a composed 65. Unfortunately for Guyana, he could not kick on to get three figures, while Travis Dowlin was snared by Amit Jaggernauth for 31. Deonarine held fort until stumps with 33 and will look to extend his 34-run association with Vishaul Singh on the third day.
Jamaica's batsmen drove home the advantage created by their bowlers as they finished the second day 190 runs clear of Leewards Islands with two second innings wickets intact at Warner Park. Resuming at a precarious 39 for 2, the Jamaican batsmen avoided the errors made by their counterparts from Leewards and got their eye in on a wicket that yielded good returns for set batsmen. Night-watchman Daren Powell did not last long, but Donovan Pagon and Tamar Lambert dug in to add 79 for the fourth wicket, before Pagon was caught by bowler Lionel Baker off a leading edge. Brendan Nash was dismissed before the first-innings lead was secured and Lambert followed soon after, raising the hopes of the Leewards' attack. But Wavell Hinds and David Bernard joined forces to deny Leewards, adding 87 runs before Gavin Tonge had Bernard edging a lifter to slip. Kieran Powell pulled off a screamer at cover to send back top-scorer Hinds for 70, but once again Jamaica found a way to shut the door on Leewards. The final act of defiance was led by Carlton Baugh's brisk counter-attacking 56 that came off 57 balls. His ninth-wicket stand with Nikita Miller was worth 63 at stumps, leaving Baker and Tonge frustrated on a day when they led the Leewards' attack, picking seven wickets between them.
Barbados threatened to shut Combined Campuses and Colleges completely out of the match, but their progress was checked by an inspired final-session comeback led by offspinner Ryan Austin as they finished the second day with a first-innings lead of 88 in Charlestown. Jason Haynes gave Barbados the early advantage with a stroke-filled 52 off 123 balls, including four fours and two sixes. CCC only managed one wicket, that of night-watchman Nikolai Charles for 20, in the first session. Kirk Edwards and Ryan Hinds failed to convert their starts, as Gavin Wallace reduced Barbados to 189 for 5 before Kevin Stoute and Sharmarh Brooks steadied the innings with a 70-run stand. Stoute struck nine classy fours off 104 balls, as he top-scored with 74, before he edged Kevin Kantasingh's left-arm spin to slip. That was the opening CCC were looking for and Austin helped them to elbow their way back into the match, as he polished off the tail, picking 4 for 87 in the process.