Phong độ của Cunupia FC |
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| 11.06.2023 | Central FC | 3-1 | Cunupia FC |  | ||
| 04.06.2023 | Cunupia FC(N) | 0-2 | Point Fortin FC | | ||
| 29.05.2023 | AC Port Of Spain | 4-0 | Cunupia FC | | ||
| 14.05.2023 | Cunupia FC | 0-2 | National Defense Forces | | ||
| 11.05.2023 | Club Sando | 1-0 | Cunupia FC | | ||
| 01.05.2023 | Cunupia FC | 0-3 | Williams Connection | | ||
| 27.04.2023 | Cunupia FC | 1-4 | Club Sando | | ||
| 17.04.2023 | National Defense Forces | 1-0 | Cunupia FC | | ||
| 13.03.2023 | Caledonia AIA | 2-0 | Cunupia FC | | ||
Phong độ của Prison Service FC |
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| 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 | | ||
| 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 | | ||