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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Windward Islands vs Combined Campuses and Colleges | 9th Match | 12-Feb-2025 | Dominica | 4 Day Match |
| Trinidad & Tobago vs Windward Islands | 8th Match | 05-Feb-2025 | Kingstown | 4 Day Match |
| Jamaica vs Windward Islands | 3rd Match | 29-Jan-2025 | Kingstown | 4 Day Match |
| Windward Islands vs Combined Campuses and Colleges | 24th Match | 13-Nov-2024 | Tarouba | 50 Over Match |
| Barbados Royals vs Windward Islands | 20th Match | 11-Nov-2024 | Port of Spain | 50 Over Match |
| Leeward Islands vs Windward Islands | 16th Match | 08-Nov-2024 | St Augustine | 50 Over Match |
| Jamaica vs Windward Islands | 12th Match | 05-Nov-2024 | Port of Spain | 50 Over Match |