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| Match | Bat | Date | Ground | Format |
|---|---|---|---|---|
| Trinidad & Tobago (w) vs Windward Islands (w) | 1st Match | 27-Jan-2026 | - | 50 Over Match |
| Jamaica (w) vs Windward Islands (w) | 16th Match | 23-Jan-2026 | Kingstown | T20 |
| Barbados (w) vs Windward Islands (w) | 2nd Match | 17-Jan-2026 | Kingstown | T20 |