| Windward Islands vs Barbados Royals | 23rd Match | 02-Apr-2025 | Gros Islet, St Lucia | 4 Day Match |
| Windward Islands vs Guyana Amazon Warriors | 17th Match | 12-Mar-2025 | Guyana | 4 Day Match |
| Windward Islands vs Leeward Islands | 14th Match | 05-Mar-2025 | Gros Islet, St Lucia | 4 Day Match |
| 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 West Indies Academy | 28th Match | 17-Nov-2024 | St Augustine | 50 Over 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 |
| Windward Islands vs Trinidad & Tobago | 7th Match | 01-Nov-2024 | Tarouba | 50 Over Match |
| Guyana Amazon Warriors vs Windward Islands | 2nd Match | 29-Oct-2024 | Tarouba | 50 Over Match |
