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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| 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 |
| Windward Islands (w) vs Leeward Islands (w) | 5th.Place.Play.off.Semi.Final | 07-Mar-2025 | Basseterre | 50 Over Match |
| Windward Islands (w) vs Jamaica (w) | 13th Match | 05-Mar-2025 | Basseterre | 50 Over Match |
| Barbados (w) vs Windward Islands (w) | 6th Match | 26-Feb-2025 | Basseterre, St Kitts | 50 Over Match |
| Windward Islands (w) vs Leeward Islands (w) | 2nd Match | 24-Feb-2025 | Basseterre | 50 Over Match |