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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Trinidad & Tobago (w) vs Windward Islands (w) | 1st Match | 27-Jan-2026 | - | 50 Over Match |
| Jamaica (w) vs Windward Islands (w) | 16th Match | 23-Jan-2026 | Kingstown | T20 |
| Barbados (w) vs Windward Islands (w) | 2nd Match | 17-Jan-2026 | Kingstown | T20 |
| Windward Islands (w) vs Trinidad & Tobago (w) | 1st Match | 15-Jan-2026 | Kingstown | T20 |
| Windward Islands (w) vs Barbados (w) | 15th Match | 09-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 |
| 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 |
| Sri Lanka U19 (W) vs West Indies U19 (W) | 15th Match | 21-Jan-2025 | Kuala Lumpur | Youth T20 |
| West Indies U19 (W) vs India U19 (W) | 8th Match | 19-Jan-2025 | Kuala Lumpur | Youth T20 |