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Trinidad & Tobago
| 19.03.2026 | D1 | Caledonia AIA FC | 0-2 | AC Port of Spain | |
| 10.12.2025 | D1 | Caledonia AIA FC | 3-2 | AC Port of Spain | |
| 31.03.2025 | D1 | Caledonia AIA FC | 1-1 | AC Port of Spain | |
| 16.12.2024 | D1 | AC Port of Spain | 0-1 | Caledonia AIA FC | |
| 19.02.2024 | D1 | AC Port of Spain | 3-3 | Caledonia AIA FC | |
| 26.11.2023 | D1 | Caledonia AIA FC | 0-2 | AC Port of Spain |
| 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 | 37.04% | 20 |
| draw | 22.22% | 12 |
| Caledonia AIA lose | 40.74% | 22 |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 3 | 0 | 3 | 10 | 11 | -1 |
| away | 6 | 4 | 1 | 1 | 12 | 7 | 5 |
| total | 6 | 3 | 0 | 3 | 8 | 10 | -2 |
| Port of Spain win | 40.74% | 22 |
| draw | 22.22% | 12 |
| Port of Spain lose | 37.04% | 20 |
| 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 | |
| 29.03.2026 | D1 | Defence Force | 2-0 | AC Port of Spain | |
| 21.03.2026 | D1 | AC Port of Spain | 1-4 | San Juan Jabloteh | |
| 19.03.2026 | D1 | Caledonia AIA FC | 0-2 | AC Port of Spain | |
| 13.03.2026 | D1 | AC Port of Spain | 0-2 | Eagles FC (T&T) | |
| 11.03.2026 | D1 | AC Port of Spain | 1-0 | Police FC (T&T) | |
| 28.02.2026 | D1 | Point Fortin Civic | 2-4 | AC Port of Spain | |
| over 2.5 | 63.64% | 14 |
| under 2.5 | 36.36% | 8 |
| over 2.5 | 61.54% | 16 |
| under 2.5 | 38.46% | 10 |
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