Lịch sử đối đầu Prison Service FC vs Caledonia AIA |
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| 12.06.2023 | Caledonia AIA(N) | 3-1 | Prison Service FC |  | |
Phong độ của Prison Service FC |
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| 07.01.2024 | Point Fortin FC | 2-1 | Prison Service FC | | ||
| 04.01.2024 | Prison Service FC | 0-3 | Club Sando | | ||
| 18.12.2023 | Trinidad Tobago Police FC | 7-0 | Prison Service FC | | ||
| 09.12.2023 | Prison Service FC | 1-3 | National Defense Forces | | ||
| 04.12.2023 | Cunupia FC | 1-2 | Prison Service FC | | ||
| 27.11.2023 | Prison Service FC | 4-1 | Central FC | | ||
| 15.06.2023 | Point Fortin FC | 2-2 | Prison Service FC | | ||
| 12.06.2023 | Caledonia AIA(N) | 3-1 | Prison Service FC | | ||
| 29.05.2023 | La Horquetta Rangers FC | 4-1 | Prison Service FC | | ||
| 20.05.2023 | National Defense Forces | 4-1 | Prison Service FC | | ||
Phong độ của Caledonia AIA |
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| 07.01.2024 | Caledonia AIA | 1-2 | Trinidad Tobago Police FC | | ||
| 04.01.2024 | National Defense Forces | 2-1 | Caledonia AIA | | ||
| 21.12.2023 | Caledonia AIA | 2-0 | Cunupia FC | | ||
| 16.12.2023 | Central FC | 1-3 | Caledonia AIA | | ||
| 02.12.2023 | La Horquetta Rangers FC | 3-1 | Caledonia AIA | | ||
| 27.11.2023 | Caledonia AIA | 0-2 | AC Port Of Spain | | ||
| 12.06.2023 | Caledonia AIA(N) | 3-1 | Prison Service FC | | ||
| 14.05.2023 | Caledonia AIA | 3-2 | La Horquetta Rangers FC | | ||
| 04.05.2023 | Club Sando | 3-1 | Caledonia AIA | | ||
| 24.04.2023 | National Defense Forces | 5-0 | Caledonia AIA | | ||