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| Date | Match | Score |
|---|---|---|
| 19.11.2025 | Cunupia - Prison Service | 0 : 1 |
| 02.05.2025 | Cunupia - Prison Service | 1 : 0 |
| 18.01.2025 | Prison Service - Cunupia | 2 : 4 |
| 25.02.2024 | Prison Service - Cunupia | 0 : 3 |
| 03.12.2023 | Cunupia - Prison Service | 1 : 2 |
| 06.05.2023 | Cunupia - Prison Service | 0 : 2 |
| 22.04.2023 | Prison Service - Cunupia | 1 : 1 |
| 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 |
|---|---|---|---|
| 28.03.2026 | Club Sando - Cunupia | 0 - 0 | D |
| 25.03.2026 | Cunupia - Point Fortin | 0 - 0 | D |
| 20.03.2026 | Cunupia - Defence Force | 0 - 0 | D |
| 13.03.2026 | Cunupia - Athletic Club | 0 - 2 | L |
| 07.03.2026 | Prison Service - Cunupia | 1 - 3 | W |