| West Indies Championship | 04/17 14:00 | - | Wyspy Podwietrzne v Windward Islands | View | |
| West Indies Championship | 04/10 14:00 | - | West Indies Academy v Windward Islands | View | |
| West Indies Championship | 03/20 14:00 | - | Guyana v Windward Islands | View | |
| West Indies Championship | 03/13 14:00 | - | Trynidad i Tobago v Windward Islands | View | |
| West Indies Championship | 02/21 14:00 | - | Windward Islands v Combined Campuses & Colleges | View | |
| West Indies Championship | 02/14 15:00 | - | Barbados v Windward Islands | View | |
| West Indies Championship | 02/07 15:00 | - | Jamajka v Windward Islands | View | |
| Regional Super50 | 11/03 13:00 | - | West Indies Academy v Windward Islands | CANC | |
| Regional Super50 | 10/31 13:00 | - | Windward Islands v Wyspy Podwietrzne | 179/10(42.3)-293/10(50) | |
| Regional Super50 | 10/29 17:00 | - | Jamajka v Windward Islands | 158/10(42.2)-159/6(36.2) | |
| Regional Super50 | 10/25 13:00 | - | Windward Islands v Barbados | 241/8(50)-148/2(14.5) | |
| Regional Super50 | 10/22 13:00 | - | Windward Islands v Combined Campuses & Colleges | 267/8(50)-271/8(50) |