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Trinidad & Tobago
| 27.03.2026 | D1 | Prison Service FC | 1-0 | Caledonia AIA FC | |
| 25.10.2025 | D1 | Prison Service FC | 3-2 | Caledonia AIA FC | |
| 17.05.2025 | D1 | Caledonia AIA FC | 2-1 | Prison Service FC | |
| 02.02.2025 | D1 | Prison Service FC | 1-2 | Caledonia AIA FC | |
| 07.04.2024 | D1 | Caledonia AIA FC | 1-0 | Prison Service FC | |
| 14.01.2024 | D1 | Prison Service FC | 2-1 | Caledonia AIA FC |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 0 | 0 | 6 | 1 | 14 | -13 |
| away | 6 | 2 | 0 | 4 | 9 | 11 | -2 |
| total | 6 | 1 | 0 | 5 | 6 | 12 | -6 |
| Caledonia AIA win | 50.00% | 4 |
| draw | % | 0 |
| Caledonia AIA lose | 50.00% | 4 |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 5 | 0 | 1 | 15 | 7 | 8 |
| away | 6 | 3 | 1 | 2 | 10 | 9 | 1 |
| total | 6 | 6 | 0 | 0 | 16 | 5 | 11 |
| Prison Service win | 50.00% | 4 |
| draw | % | 0 |
| Prison Service lose | 50.00% | 4 |
| 27.03.2026 | D1 | Prison Service FC | 1-0 | Caledonia AIA FC |  |
| 22.03.2026 | D1 | Caledonia AIA FC | 0-5 | Club Sando | |
| 19.03.2026 | D1 | Caledonia AIA FC | 0-2 | AC Port of Spain | |
| 14.03.2026 | D1 | Caledonia AIA FC | 1-2 | La Horquetta Rangers | |
| 07.03.2026 | D1 | Central FC (T&T) | 1-5 | Caledonia AIA FC |  |
| 01.03.2026 | D1 | Caledonia AIA FC | 0-1 | San Juan Jabloteh | |
| 27.03.2026 | D1 | Prison Service FC | 1-0 | Caledonia AIA FC | |
| 22.03.2026 | D1 | 1976 FC Phoenix | 2-5 | Prison Service FC | |
| 18.03.2026 | D1 | Prison Service FC | 2-1 | San Juan Jabloteh | |
| 15.03.2026 | D1 | Club Sando | 0-1 | Prison Service FC | |
| 07.03.2026 | D1 | Eagles FC (T&T) | 1-3 | Prison Service FC | |
| 28.02.2026 | D1 | Prison Service FC | 4-1 | La Horquetta Rangers | |
| over 2.5 | 63.64% | 14 |
| under 2.5 | 36.36% | 8 |
| over 2.5 | 59.09% | 13 |
| under 2.5 | 40.91% | 9 |
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