Stadium: Queen's Park Oval
| Regional Super50 | 2022/11/12 18:00 | Trinidad & Tobago v Windward Islands | 249-201 |
| Regional Super50 | 2022/11/05 13:00 | Trinidad & Tobago v Windward Islands | 195-189 |
| Regional Super50 | 2021/02/13 17:30 | Windward Islands v Trinidad & Tobago | 227-228 |
| Plunket Shield | 2019/11/17 17:30 | Trinidad & Tobago v Windward Islands | 179/10(28.3)-177/10(28.3) |
| Plunket Shield | 2019/11/07 17:30 | Trinidad & Tobago v Windward Islands | 239/2(42.5)-238/8(50) |
| Plunket Shield | 2018/10/17 18:00 | Windward Islands v Trinidad & Tobago | 78 All Out,83/3 |
| Plunket Shield | 2017/02/06 17:21 | Trinidad & Tobago v Windward Islands | 214 All Out,182/9 |
| Regional Super50 | 2023/10/17 13:00 | Trinidad & Tobago v Combined Campuses & Colleges | 246-53 |
| West Indies Championship | 2023/03/29 14:00 | Trinidad & Tobago v Jamaica | /()-/() |
| West Indies Championship | 2023/03/22 14:00 | Trinidad & Tobago v Barbados | /()-/() |
| West Indies Championship | 2023/03/15 14:00 | Trinidad & Tobago v Guyana | /()-/() |
| West Indies Championship | 2023/02/08 14:00 | Leeward Islands v Trinidad & Tobago | 302/10(100.1)-418/9(126.5) |
| Regional Super50 | 2022/11/19 18:00 | Trinidad & Tobago v Jamaica | 217-218 |
| Regional Super50 | 2022/11/16 18:00 | Trinidad & Tobago v Barbados | 312-303 |
| Regional Super50 | 2022/11/12 18:00 | Trinidad & Tobago v Windward Islands | 249-201 |
| Regional Super50 | 2023/10/17 17:00 | Guyana v Windward Islands | 229/9(50)-219/10(46) |
| West Indies Championship | 2023/03/29 14:00 | Barbados v Windward Islands | /()-/() |
| West Indies Championship | 2023/03/22 14:00 | Leeward Islands v Windward Islands | /()-/() |
| West Indies Championship | 2023/03/15 14:00 | Jamaica v Windward Islands | /()-/() |
| West Indies Championship | 2023/02/08 14:00 | Windward Islands v Guyana | 294/10(80.5)-169/10(63.1) |
| Regional Super50 | 2022/11/12 18:00 | Trinidad & Tobago v Windward Islands | 249-201 |
| Regional Super50 | 2022/11/09 18:00 | Combined Campuses & Colleges v Windward Islands | 180-277 |
| Regional Super50 | 2022/11/07 18:00 | Guyana v Windward Islands | 190-129 |