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| Date | Match | Score |
|---|---|---|
| 23.11.2025 | La Horquetta Rangers - Prison Service | 0 : 1 |
| 26.04.2025 | Prison Service - La Horquetta Rangers | 2 : 2 |
| 12.01.2025 | Prison Service - La Horquetta Rangers | 0 : 0 |
| 10.05.2024 | La Horquetta Rangers - Prison Service | 2 : 1 |
| 28.01.2024 | Prison Service - La Horquetta Rangers | 1 : 3 |
| 28.05.2023 | La Horquetta Rangers - Prison Service | 4 : 1 |
| 31.03.2023 | Prison Service - La Horquetta Rangers | 0 : 2 |
| 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 |
| Date | Match | Score | Res |
|---|---|---|---|
| 27.03.2026 | Phoenix - La Horquetta Rangers | 1 - 0 | L |
| 21.03.2026 | La Horquetta Rangers - Point Fortin | 0 - 1 | L |
| 18.03.2026 | Central - La Horquetta Rangers | 0 - 0 | D |
| 14.03.2026 | La Horquetta Rangers - Morvant Caledonia United | 1 - 2 | L |
| 07.03.2026 | Club Sando - La Horquetta Rangers | 0 - 3 | W |