All countries
| 6. Round | Mount Pleasant | Portmore | details | Today 21:00 | |||
| 9. Round | Mount Pleasant | Tivoli | 2:1 (0:1, 2:0) | details | 08.11.2026 | |||
| 5. Round | Arnett Gardens | Mount Pleasant | 1:1 (0:0, 1:1) | details | 06.11.2026 | |||
| 8. Round | Molynes | Mount Pleasant | 1:2 (0:1, 1:1) | details | 02.11.2026 | |||
| 7. Round | Mount Pleasant | Montego Bay | 2:1 (0:1, 2:0) | details | 27.10.2026 | |||
| Semi-finals - Second leg | Mount Pleasant | Sando | 2:0 (0:0, 2:0) | details | 23.10.2026 | |||
| 6. Round | Mount Pleasant | Portmore | details | Today 21:00 | |||
| Final - First leg | Portmore | Mount Pleasant | details | 02.12.2026 01:00 | |||
| Final - Second leg | Mount Pleasant | Portmore | details | 06.12.2026 01:00 | |||