All countries
| 7. Round | Prison Service | San Juan Jabloteh | details | 08.12.2025 00:00 | |||
| 6. Round | Central FC | Prison Service | 1:0 (0:0, 1:0) | details | 30.11.2025 | |||
| 5. Round | La Horquetta | Prison Service | 0:1 (0:0, 0:1) | details | 24.11.2025 | |||
| 4. Round | Eagles FC | Prison Service | 0:1 | details | 19.11.2025 | |||
| 3. Round | Sando | Prison Service | 0:1 (0:0, 0:1) | details | 09.11.2025 | |||
| 2. Round | 1976 Phoenix FC | Prison Service | 0:4 (0:0, 0:4) | details | 02.11.2025 | |||
| 7. Round | Prison Service | San Juan Jabloteh | details | 08.12.2025 00:00 | |||
| 8. Round | Defence Force | Prison Service | details | 12.12.2025 23:00 | |||
| 9. Round | Prison Service | Port Of Spain | details | 20.12.2025 22:00 | |||
| 10. Round | Police | Prison Service | details | 26.12.2025 22:00 | |||