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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Jamaica vs Windward Islands | 15th Match | 27-Nov-2025 | Tarouba | 50 Over Match |
| Barbados Royals vs Windward Islands | 8th Match | 23-Nov-2025 | Port of Spain | 50 Over Match |
| Leeward Islands vs Windward Islands | 2nd Match | 19-Nov-2025 | Tarouba | 50 Over Match |
| West Indies A vs South Africa A | 3rd Match | 27-May-2025 | Gros Islet, St Lucia | List A ODI |
| South Africa A vs West Indies A | 1st Match | 21-May-2025 | Gros Islet, St Lucia | List A ODI |
| Clove Challengers vs Saffron Strikers | 2nd Match | 12-May-2025 | Grenada | 10 Over Match |
| Windward Islands vs Leeward Islands | Play Off | 09-May-2025 | Tarouba | T20 |
| Windward Islands vs Leeward Islands | 15th Match | 07-May-2025 | Tarouba | T20 |
| Windward Islands vs Jamaica | 14th Match | 06-May-2025 | Tarouba | T20 |
| Windward Islands vs Trinidad & Tobago | 11th Match | 04-May-2025 | Tarouba | T20 |
| Barbados Royals vs Windward Islands | 6th Match | 29-Apr-2025 | Tarouba | T20 |
| Windward Islands vs Guyana Amazon Warriors | 1st Match | 25-Apr-2025 | Tarouba | T20 |
| Botanical Gardens Rangers vs Grenadines Divers | Final | 21-Apr-2025 | Kingstown | 10 Over Match |
| La Soufriere Hikers vs Botanical Gardens Rangers | Qualifier 2 | 20-Apr-2025 | Kingstown | 10 Over Match |
| Dark View Explorers vs Botanical Gardens Rangers | Eliminator | 18-Apr-2025 | Kingstown | 10 Over Match |
| Grenadines Divers vs Botanical Gardens Rangers | 23rd Match | 17-Apr-2025 | Kingstown | 10 Over Match |
| Botanical Gardens Rangers vs Salt Pond Breakers | 20th Match | 15-Apr-2025 | Kingstown | 10 Over Match |
| Botanical Gardens Rangers vs Fort Charlotte Strikers | 18th Match | 14-Apr-2025 | Kingstown | 10 Over Match |
| Salt Pond Breakers vs Botanical Gardens Rangers | 15th Match | 13-Apr-2025 | Kingstown | 10 Over Match |
| Dark View Explorers vs Botanical Gardens Rangers | 14th Match | 12-Apr-2025 | Kingstown | 10 Over Match |
| Grenadines Divers vs Botanical Gardens Rangers | 10th Match | 11-Apr-2025 | Kingstown | 10 Over Match |
| Windward Islands vs West Indies Academy | 28th Match | 09-Apr-2025 | North sound | 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 |
| Jamaica vs Windward Islands | 12th Match | 05-Nov-2024 | Port of Spain | 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 |