All countries
| Final - First leg | Portmore | Mount Pleasant | details | 02.12.2026 01:00 | |||
| 8. Round | Montego Bay | Portmore | 2:2 (1:1, 1:1) | details | 01.11.2026 | |||
| Semi-finals - Second leg | Violette | Portmore | 2:1 (0:1, 2:0) | details | 29.10.2026 | |||
| 7. Round | Portmore | Chapelton | 0:0 (0:0, 0:0) | details | 25.10.2026 | |||
| 6. Round | Mount Pleasant | Portmore | POSTP. | details | 18.10.2026 | |||
| Semi-finals - First leg | Portmore | Violette | 3:1 (0:1, 3:0) | details | 14.10.2026 | |||
| Final - First leg | Portmore | Mount Pleasant | details | 02.12.2026 01:00 | |||