All countries
| Final - 2nd leg | Mount Pleasant | Universidad O&M | details | 03.12.2025 01:00 | |||
| Final - 1st leg | Universidad O&M | Mount Pleasant | 0:1 (0:1, 0:0) | details | 26.11.2025 | |||
| Semi-finals - 2nd leg | Mount Pleasant | Defence Force | 0:1 (0:1, 0:0) | details | 06.11.2025 | |||
| Semi-finals - 1st leg | Defence Force | Mount Pleasant | 1:5 (0:2, 1:3) | details | 23.10.2025 | |||
| 9. Round | Mount Pleasant | Treasure Beach | POSTP. | details | 19.10.2025 | |||
| 8. Round | Mount Pleasant | Chapelton | 3:1 (2:1, 1:0) | details | 12.10.2025 | |||
| Final - 2nd leg | Mount Pleasant | Universidad O&M | details | 03.12.2025 01:00 | |||
| 10. Round | Dunbeholden | Mount Pleasant | details | 07.12.2025 21:00 | |||
| 11. Round | Mount Pleasant | Tivoli | details | 11.12.2025 21:00 | |||
| 12. Round | Portmore | Mount Pleasant | details | 14.12.2025 21:00 | |||
| 3. Round | Racing United | Mount Pleasant | details | 17.12.2025 21:00 | |||
| 13. Round | Mount Pleasant | Spanish Town Police | details | 21.12.2025 21:00 | |||