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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Leeward Islands vs Barbados Royals | 26th Match | 09-Apr-2025 | Basseterre, St Kitts | 4 Day Match |
| Guyana Amazon Warriors vs Leeward Islands | 21st Match | 02-Apr-2025 | Basseterre, St Kitts | 4 Day Match |
| Leeward Islands vs Combined Campuses and Colleges | 19th Match | 12-Mar-2025 | North sound | 4 Day Match |
| Windward Islands vs Leeward Islands | 14th Match | 05-Mar-2025 | Gros Islet, St Lucia | 4 Day Match |
| Leeward Islands vs Trinidad & Tobago | 11th Match | 12-Feb-2025 | Basseterre, St Kitts | 4 Day Match |
| Jamaica vs Leeward Islands | 6th Match | 05-Feb-2025 | North sound | 4 Day Match |
| Leeward Islands vs West Indies Academy | 2nd Match | 29-Jan-2025 | Antigua | 4 Day Match |
| Jamaica vs Leeward Islands | 2nd Semi-Final | 21-Nov-2024 | Tarouba | 50 Over Match |
| Combined Campuses and Colleges vs Leeward Islands | 27th Match | 17-Nov-2024 | Port of Spain | 50 Over Match |
| Jamaica vs Leeward Islands | 25th Match | 15-Nov-2024 | Tarouba | 50 Over Match |