| 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 |
| 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 |
| Guyana (w) vs Windward Islands (w) | 11th Match | 03-Mar-2025 | Basseterre | 50 Over Match |
| Trinidad & Tobago (w) vs Windward Islands (w) | 7th Match | 28-Feb-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 |
