Head to Head
| Regional Super50 | 2023/11/11 17:00 | Trinidad & Tobago v Leeward Islands | 141/3(23.4)-135/10(41.5) |
| Regional Super50 | 2023/10/26 17:00 | Trinidad & Tobago v Leeward Islands | 199-198 |
| West Indies Championship | 2023/02/08 14:00 | Leeward Islands v Trinidad & Tobago | 302/10(100.1)-418/9(126.5) |
| Regional Super50 | 2021/02/17 17:30 | Leeward Islands v Trinidad & Tobago | 129-130 |
| Plunket Shield | 2019/11/29 17:30 | Trinidad & Tobago v Leeward Islands | 268/8(50)-269/6(49.3) |
| Plunket Shield | 2017/02/12 17:12 | Leeward Islands v Trinidad & Tobago | 190 All Out,191/5 |
| Plunket Shield | 2017/02/02 17:34 | Leeward Islands v Trinidad & Tobago | 215/9,226/9 |
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 | 239-173 |
| Regional Super50 | 2023/10/18 17:00 | Leeward Islands v Jamaica | 124-123 |
Away History
| Regional Super50 | 2023/11/11 17:00 | Trinidad & Tobago v Leeward Islands | 141/3(23.4)-135/10(41.5) |
| Regional Super50 | 2023/11/08 17:00 | Trinidad & Tobago v Guyana | 107/4(27.4)-105/10(34.3) |
| Regional Super50 | 2023/11/05 17:00 | Trinidad & Tobago v Barbados | 293-215 |
| Regional Super50 | 2023/10/28 13:00 | Trinidad & Tobago v West Indies Academy | 264-263 |
| Regional Super50 | 2023/10/26 17:00 | Trinidad & Tobago v Leeward Islands | 199-198 |
| Regional Super50 | 2023/10/21 17:00 | Trinidad & Tobago v Guyana | 290-176 |
| Regional Super50 | 2023/10/19 13:00 | Trinidad & Tobago v Windward Islands | 255-254 |
| Regional Super50 | 2023/10/17 13:00 | Trinidad & Tobago v Combined Campuses & Colleges | 246-53 |