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| Date | Match | Score |
|---|---|---|
| 11.01.2026 | Prison Service - Point Fortin | 3 : 1 |
| 03.01.2026 | Prison Service - Point Fortin | 3 : 1 |
| 29.03.2025 | Point Fortin - Prison Service | 0 : 3 |
| 14.12.2024 | Prison Service - Point Fortin | 2 : 0 |
| 04.04.2024 | Prison Service - Point Fortin | 0 : 1 |
| 06.01.2024 | Point Fortin - Prison Service | 2 : 1 |
| 14.06.2023 | Point Fortin - Prison Service | 2 : 2 |
| 18.03.2023 | Prison Service - Point Fortin | 0 : 2 |
| Date | Match | Score | Res |
|---|---|---|---|
| 29.03.2026 | Point Fortin - Central | 0 - 0 | D |
| 25.03.2026 | Cunupia - Point Fortin | 0 - 0 | D |
| 21.03.2026 | La Horquetta Rangers - Point Fortin | 0 - 1 | W |
| 14.03.2026 | San Juan Jabloteh - Point Fortin | 1 - 5 | W |
| 07.03.2026 | Point Fortin - Defence Force | 2 - 2 | D |
| Date | Match | Score | Res |
|---|---|---|---|
| 27.03.2026 | Morvant Caledonia United - Prison Service | 1 - 0 | L |
| 22.03.2026 | Prison Service - Phoenix | 0 - 0 | D |
| 18.03.2026 | San Juan Jabloteh - Prison Service | 2 - 1 | L |
| 15.03.2026 | Prison Service - Club Sando | 0 - 1 | L |
| 07.03.2026 | Prison Service - Cunupia | 1 - 3 | L |