Combined Campuses and Colleges (CCC) secured a four-wicket victory against Leeward Islands according to the D/L method in a rain-shortened match in Georgetown. The victory was set up by CCC's left-arm spinner, Kavesh Kantasingh, who took the new ball and claimed a career best 6 for 26. His spell helped dismiss Leeward Islands for 174 in 49 overs. Jahmar Hamilton top scored with 45. Rain during CCC's innings reduced their target to 148 in 34 overs and they achieved it with five balls to spare. CCC were reduced to 56 for 4 at one stage but Floyd Reifer scored an unbeaten 52 and Kyle Mayers made 31 to secure the victory. Legspinner Anthony Martin claimed 3 for 26 for Leeward Islands. Both teams failed to qualify for the semi-finals.

Offspinner Sunil Narine took 5 for 37 to lead Trinidad & Tobago to a 36-run victory against Jamaica in another rain-hit contest at the Providence Stadium. The result secured T&T a place in the semi-finals of the Regional Super50. T&T were able to bat all their 50 overs but managed to score only 196, with Dwayne Bravo top scoring with 55. They were 154 for 4 at one stage before losing six wickets for 42 runs. Jamaica's left-arm spinner Nikita Miller took 3 for 32. Jamaica's innings was reduced to 40 overs and the D/L target was set at 191. Chris Gayle made 31 but he was one of Narine's five top-order victims as the innings slumped to 46 for 5. Tamar Lambert was unbeaten on 48 and Andre Russell made 31 but they were the only batsmen, along with Gayle, to reach double figures. Jamaica could make only 154 for 9 in 40 overs.