Stadium: Brian Lara Stadium
| West Indies Championship | 2023/03/15 14:00 | Jamaica v Windward Islands | /()-/() |
| Regional Super50 | 2021/02/16 17:30 | Windward Islands v Jamaica | 260-168 |
| Regional Super50 | 2023/10/27 13:00 | Jamaica v Combined Campuses & Colleges | 198/10(32.4)-320/7(48) |
| Regional Super50 | 2023/10/25 13:00 | West Indies Academy v Jamaica | 227/4(37.3)-263/9(50) |
| Regional Super50 | 2023/10/20 13:00 | Barbados v Jamaica | 258/6(50)-211/10(44.3) |
| Regional Super50 | 2023/10/18 17:00 | Leeward Islands v Jamaica | 124/2(14)-123/10(32.5) |
| West Indies Championship | 2023/03/29 14:00 | Trinidad & Tobago v Jamaica | /()-/() |
| West Indies Championship | 2023/03/22 14:00 | Guyana v Jamaica | /()-/() |
| West Indies Championship | 2023/03/15 14:00 | Jamaica v Windward Islands | /()-/() |
| West Indies Championship | 2023/02/08 14:00 | Jamaica v Barbados | 140/10(54.5)-215/10(69.5) |
| Regional Super50 | 2023/10/25 13:00 | Windward Islands v Barbados | 241/8(50)-148/2(14.5) |
| Regional Super50 | 2023/10/22 13:00 | Windward Islands v Combined Campuses & Colleges | 267/8(50)-271/8(50) |
| Regional Super50 | 2023/10/19 13:00 | Trinidad & Tobago v Windward Islands | 255/4(48)-254/9(50) |
| 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) |