| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Trinidad & Tobago vs Leeward Islands | Final | 10-May-2025 | Tarouba | T20 |
| Windward Islands vs Leeward Islands | Play Off | 09-May-2025 | Tarouba | T20 |
| Windward Islands vs Leeward Islands | 15th Match | 07-May-2025 | Tarouba | T20 |
| Guyana Amazon Warriors vs Leeward Islands | 12th Match | 04-May-2025 | Tarouba | T20 |
| Trinidad & Tobago vs Leeward Islands | 10th Match | 02-May-2025 | Tarouba | T20 |
| Barbados Royals vs Leeward Islands | 8th Match | 30-Apr-2025 | Tarouba | T20 |
| Jamaica vs Leeward Islands | 3rd Match | 26-Apr-2025 | Tarouba | T20 |