Phong độ của Harbour View FC |
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| 21.09.2023 | Atletico Pantoja | 1-1 | Harbour View FC |  | ||
| 24.08.2023 | Harbour View FC | 1-0 | Dunbeholden FC | | ||
| 12.06.2023 | Arnett Gardens | 0-0 | Harbour View FC | | ||
| 05.06.2023 | Cavalier FC | 2-0 | Harbour View FC | | ||
| 30.05.2023 | Harbour View FC | 0-1 | Cavalier FC | | ||
| 27.05.2023 | Harbour View FC | 0-1 | Dunbeholden FC | | ||
| 23.05.2023 | Harbour View FC | 2-3 | Humble Lions | | ||
| 20.05.2023 | Portmore United(N) | 1-1 | Harbour View FC | | ||
| 16.05.2023 | Humble Lions | 0-2 | Harbour View FC | | ||
| 13.05.2023 | Harbour View FC | 2-2 | Portmore United | | ||
Phong độ của SV Robinhood |
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| 22.09.2023 | Dunbeholden FC | 0-2 | SV Robinhood | | ||
| 01.09.2023 | SV Robinhood | 1-0 | Cibao FC | | ||
| 14.08.2023 | SV Robinhood | 5-1 | Golden Lion | | ||
| 12.08.2023 | SV Robinhood | 5-0 | Metropolitan FA | | ||
| 09.08.2023 | AS Etoile Matoury | 2-4 | SV Robinhood | | ||
| 07.08.2023 | B1 FC Castries | 0-5 | SV Robinhood | | ||
| 05.08.2023 | UniversidadO M | 1-2 | SV Robinhood | | ||