Phong độ của Caledonia AIA |
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| 15.06.2023 | Caledonia AIA | 0-1 | Central FC |  | ||
| 12.06.2023 | Caledonia AIA(N) | 3-1 | Prison Service FC | | ||
| 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 AC Port Of Spain |
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| 29.09.2023 | AC Port Of Spain | 1-1 | National Defense Forces | | ||
| 21.09.2023 | AC Port Of Spain | 2-3 | Golden Lion | | ||
| 01.09.2023 | Cavalier FC | 2-1 | AC Port Of Spain | | ||
| 25.08.2023 | Moca FC | 1-0 | AC Port Of Spain | | ||
| 11.06.2023 | Trinidad Tobago Police FC(N) | 1-1 | AC Port Of Spain | | ||
| 26.05.2023 | Central FC | 2-3 | AC Port Of Spain | | ||
| 11.05.2023 | AC Port Of Spain | 2-0 | Point Fortin FC | | ||
| 04.05.2023 | La Horquetta Rangers FC | 3-2 | AC Port Of Spain | | ||
| 23.04.2023 | Williams Connection | 1-3 | AC Port Of Spain | | ||
| 16.04.2023 | AC Port Of Spain | 4-1 | San Juan Jabloteh | | ||