Phong độ của Caledonia AIA(N) |
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| 26.05.2023 | Caledonia AIA | 0-3 | Point Fortin 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 | | ||
| 16.04.2023 | La Horquetta Rangers FC | 5-0 | Caledonia AIA | | ||
| 13.03.2023 | Caledonia AIA | 2-0 | Cunupia FC | | ||
Phong độ của Prison Service FC |
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| 26.05.2023 | Prison Service FC | 1-3 | Trinidad Tobago Police FC | | ||
| 20.05.2023 | National Defense Forces | 4-1 | Prison Service FC | | ||
| 29.04.2023 | Central FC | 3-0 | Prison Service FC | | ||
| 09.04.2023 | Prison Service FC | 0-7 | National Defense Forces | | ||
| 06.04.2023 | Trinidad Tobago Police FC | 5-2 | Prison Service FC | | ||
| 01.04.2023 | Prison Service FC | 0-2 | La Horquetta Rangers FC | | ||
| 13.03.2023 | Prison Service FC | 0-0 | San Juan Jabloteh | | ||