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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Windward Islands (w) vs Barbados (w) | 15th Match | 09-May-2025 | Kingstown | T20 |
| Windward Islands (w) vs Leeward Islands (w) | 11th Match | 07-May-2025 | Kingstown | T20 |
| Trinidad & Tobago (w) vs Windward Islands (w) | 8th Match | 05-May-2025 | Kingstown | T20 |
| Windward Islands (w) vs Guyana (w) | 4th Match | 03-May-2025 | Kingstown | T20 |
| Windward Islands (w) vs Jamaica (w) | 3rd Match | 01-May-2025 | Kingstown | T20 |