Stadium: Coolidge Cricket Ground
Referee: Michael Ragoonath Home Manager: Ian Allen Away Manager: David Williams
| Cricket | 2019/11/17 17:30 | Trinidad & Tobago v Windward Islands | 179/10(28.3)-177/10(28.3) |
| Cricket | 2019/11/07 17:30 | Trinidad & Tobago v Windward Islands | 239/2(42.5)-238/8(50) |
| Cricket | 2018/10/17 18:00 | Windward Islands v Trinidad & Tobago | 78 All Out,83/3 |
| Cricket | 2017/02/06 17:21 | Trinidad & Tobago v Windward Islands | 214 All Out,182/9 |
| Regional Super50 | 2021/02/07 13:00 | Leeward Islands v Windward Islands | 253-284 |
| Cricket | 2019/11/23 17:30 | Windward Islands v USA | 241/10(45.5)-264/10(49.2) |
| Cricket | 2019/11/21 17:30 | Windward Islands v West Indies Academy | View |
| Cricket | 2019/11/19 17:30 | Guyana v Windward Islands | 294/9(50)-272/8(50) |
| Cricket | 2019/11/17 17:30 | Trinidad & Tobago v Windward Islands | 179/10(28.3)-177/10(28.3) |
| Cricket | 2019/11/15 17:30 | Guyana v Windward Islands | 260/6(41.2)-258/5(42) |
| Cricket | 2019/11/13 17:30 | Windward Islands v USA | 182/10(45.5)-225/9(50) |
| Cricket | 2019/11/11 17:30 | West Indies Academy v Windward Islands | 261/3(50)-154/10(38) |
| Regional Super50 | 2021/02/11 13:00 | Jamaica v Trinidad & Tobago | 258-259 |
| Cricket | 2019/11/29 17:30 | Trinidad & Tobago v Leeward Islands | 268/8(50)-269/6(49.3) |
| Cricket | 2019/11/25 17:30 | West Indies Academy v Trinidad & Tobago | 79/0(18.3)-78/10(27.1) |
| Cricket | 2019/11/23 17:30 | Guyana v Trinidad & Tobago | 220/4(44.3)-218/8(46) |
| Cricket | 2019/11/21 17:30 | Trinidad & Tobago v USA | 177/3(41.5)-176/9(45) |
| Cricket | 2019/11/17 17:30 | Trinidad & Tobago v Windward Islands | 179/10(28.3)-177/10(28.3) |
| Cricket | 2019/11/15 17:30 | Trinidad & Tobago v USA | 244/4(30)-201/7(30) |
| Cricket | 2019/11/13 17:30 | Trinidad & Tobago v West Indies Academy | 233/9(50)-243/10(50) |