Head to Head
| Regional Super50 | 2023/10/18 17:00 | Leeward Islands v Jamaica | 124/2(14)-123/10(32.5) |
| West Indies Championship | 2023/02/01 14:00 | Leeward Islands v Jamaica | 260/10(118.3)-234/10(82.4) |
| Regional Super50 | 2022/11/11 13:00 | Jamaica v Leeward Islands | 182-207 |
| Regional Super50 | 2022/11/01 17:00 | Leeward Islands v Jamaica | 270-202 |
| Regional Super50 | 2021/02/19 13:00 | Leeward Islands v Jamaica | 187-220 |
| Plunket Shield | 2019/11/24 13:00 | Jamaica v Leeward Islands | 255/8(50)-242/10(28.3) |
| Plunket Shield | 2019/11/10 13:00 | Jamaica v Leeward Islands | 264/2(45.4)-262/9(50) |
| Plunket Shield | 2018/10/12 13:00 | Jamaica v Leeward Islands | 214/3,214/9 |
Home History
| Regional Super50 | 2023/11/11 17:00 | Trinidad & Tobago v Leeward Islands | 141/3(23.4)-135/10(41.5) |
| Regional Super50 | 2023/11/09 17:00 | Leeward Islands v Barbados | 290/10(49.4)-135/10(30.2) |
| Regional Super50 | 2023/11/02 17:00 | Leeward Islands v Barbados | 192-196 |
| Regional Super50 | 2023/10/31 13:00 | Windward Islands v Leeward Islands | 179-293 |
| Regional Super50 | 2023/10/26 17:00 | Trinidad & Tobago v Leeward Islands | 199-198 |
| Regional Super50 | 2023/10/23 13:00 | Guyana v Leeward Islands | 248-244 |
| Regional Super50 | 2023/10/21 13:00 | Leeward Islands v West Indies Academy | 239/10(48.5)-173/10(40) |
| Regional Super50 | 2023/10/18 17:00 | Leeward Islands v Jamaica | 124/2(14)-123/10(32.5) |
Away History
| Regional Super50 | 2023/11/04 17:00 | Jamaica v Guyana | 181-184 |
| Regional Super50 | 2023/10/29 17:00 | Jamaica v Windward Islands | 158-159 |
| Regional Super50 | 2023/10/27 13:00 | Jamaica v Combined Campuses & Colleges | 198-320 |
| Regional Super50 | 2023/10/25 13:00 | West Indies Academy v Jamaica | 227-263 |
| 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 | /()-/() |