Stadium: Sir Frank Worrell Memorial Ground
| Regional Super50 | 2022/11/09 18:00 | Combined Campuses & Colleges v Windward Islands | 180-277 |
| Regional Super50 | 2022/11/02 13:00 | Combined Campuses & Colleges v Windward Islands | 109-300 |
| Regional Super50 | 2023/10/19 13:00 | Trinidad & Tobago v Windward Islands | 255-254 |
| 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 | 2023/10/19 17:00 | Combined Campuses & Colleges v West Indies Academy | 289-318 |
| Regional Super50 | 2023/10/17 13:00 | Trinidad & Tobago v Combined Campuses & Colleges | 246-53 |
| Regional Super50 | 2022/11/12 13:00 | Combined Campuses & Colleges v Guyana | 137-226 |
| Regional Super50 | 2022/11/09 18:00 | Combined Campuses & Colleges v Windward Islands | 180-277 |
| Regional Super50 | 2022/11/07 13:00 | Trinidad & Tobago v Combined Campuses & Colleges | 97-200 |
| Regional Super50 | 2022/11/05 18:00 | Guyana v Combined Campuses & Colleges | 207-206 |
| Regional Super50 | 2022/11/02 13:00 | Combined Campuses & Colleges v Windward Islands | 109-300 |
| Regional Super50 | 2022/10/31 18:00 | Trinidad & Tobago v Combined Campuses & Colleges | 120-119 |