| 21.02.2026 | D1 | Defence Force | 2-1 | Caledonia AIA FC | |
| 08.01.2026 | D1 | Defence Force | 3-1 | Caledonia AIA FC | |
| 26.04.2025 | D1 | Defence Force | 5-1 | Caledonia AIA FC | |
| 10.01.2025 | D1 | Caledonia AIA FC | 2-6 | Defence Force | |
| 28.03.2024 | D1 | Caledonia AIA FC | 1-1 | Defence Force | |
| 03.01.2024 | D1 | Defence Force | 2-1 | Caledonia AIA FC |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 4 | 1 | 1 | 14 | 8 | 6 |
| away | 6 | 2 | 1 | 3 | 10 | 14 | -4 |
| total | 6 | 3 | 1 | 2 | 15 | 6 | 9 |
| Defence Force win | 56.14% | 32 |
| draw | 15.79% | 9 |
| Defence Force lose | 28.07% | 16 |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 0 | 0 | 6 | 1 | 14 | -13 |
| away | 6 | 2 | 0 | 4 | 9 | 10 | -1 |
| total | 6 | 1 | 0 | 5 | 6 | 12 | -6 |
| Caledonia AIA win | 28.07% | 16 |
| draw | 15.79% | 9 |
| Caledonia AIA lose | 56.14% | 32 |
| 29.03.2026 | D1 | Defence Force | 2-0 | AC Port of Spain | ![]() |
| 20.03.2026 | D1 | Defence Force | 6-0 | Eagles FC (T&T) | ![]() |
| 19.03.2026 | D1 | Club Sando | 2-1 | Defence Force | ![]() |
| 15.03.2026 | D1 | Police FC (T&T) | 1-0 | Defence Force | ![]() |
| 07.03.2026 | D1 | Defence Force | 2-2 | Point Fortin Civic | ![]() |
| 04.03.2026 | D1 | 1976 FC Phoenix | 1-4 | Defence Force | ![]() |
| 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 | ![]() |
| over 2.5 | 69.70% | 23 |
| under 2.5 | 30.30% | 10 |
| over 2.5 | 63.64% | 14 |
| under 2.5 | 36.36% | 8 |
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