Phong độ của Caledonia AIA |
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| 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 | | ||
| 16.04.2023 | La Horquetta Rangers FC | 5-0 | Caledonia AIA | | ||
Phong độ của Trinidad Tobago Police FC |
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| 04.01.2024 | Trinidad Tobago Police FC | 2-1 | Point Fortin FC | | ||
| 21.12.2023 | Club Sando | 0-1 | Trinidad Tobago Police FC | | ||
| 18.12.2023 | Trinidad Tobago Police FC | 7-0 | Prison Service FC | | ||
| 12.12.2023 | Trinidad Tobago Police FC | 2-0 | FC Phoenix | | ||
| 04.12.2023 | Trinidad Tobago Police FC | 2-2 | National Defense Forces | | ||
| 25.11.2023 | Trinidad Tobago Police FC | 1-1 | Eagles FC Cochin | | ||
| 15.06.2023 | Williams Connection | 0-3 | Trinidad Tobago Police FC | | ||
| 11.06.2023 | Trinidad Tobago Police FC(N) | 1-1 | AC Port Of Spain | | ||
| 29.05.2023 | Trinidad Tobago Police FC | 2-1 | Club Sando | | ||
| 17.05.2023 | Trinidad Tobago Police FC | 0-1 | Central FC | | ||