Lịch sử đối đầu Harbour View FC vs Portmore United |
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| 20.05.2023 | Portmore United(N) | 1-1 | Harbour View FC |  | |
| 13.05.2023 | Harbour View FC | 2-2 | Portmore United | | |
| 03.04.2023 | Harbour View FC | 0-1 | Portmore United | | |
Phong độ của Harbour View FC |
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| 20.11.2023 | Mount Pleasant FA | 2-0 | Harbour View FC | | ||
| 14.11.2023 | Harbour View FC | 2-2 | Humble Lions | | ||
| 10.11.2023 | Harbour View FC | 1-3 | Cavalier FC | | ||
| 07.11.2023 | Harbour View FC | 2-2 | Arnett Gardens | | ||
| 01.11.2023 | Cavalier FC | 0-0 | Harbour View FC | | ||
| 25.10.2023 | Harbour View FC | 0-5 | Cavalier FC | | ||
| 06.10.2023 | Cibao FC | 2-1 | Harbour View FC | | ||
| 28.09.2023 | Harbour View FC | 3-2 | SV Robinhood | | ||
| 21.09.2023 | Atletico Pantoja | 1-1 | Harbour View FC | | ||
| 24.08.2023 | Harbour View FC | 1-0 | Dunbeholden FC | | ||
Phong độ của Portmore United |
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| 20.11.2023 | Portmore United | 2-0 | Molynes United | | ||
| 13.11.2023 | Dunbeholden FC | 0-2 | Portmore United | | ||
| 06.11.2023 | Portmore United | 3-1 | Treasure Beach | | ||
| 23.10.2023 | Mount Pleasant FA | 1-0 | Portmore United | | ||
| 27.05.2023 | Cavalier FC | 0-2 | Portmore United | | ||
| 20.05.2023 | Portmore United(N) | 1-1 | Harbour View FC | | ||
| 13.05.2023 | Harbour View FC | 2-2 | Portmore United | | ||
| 08.05.2023 | Molynes United | 0-3 | Portmore United | | ||
| 01.05.2023 | Portmore United | 1-1 | Waterhouse FC | | ||
| 24.04.2023 | Portmore United | 1-1 | Humble Lions | | ||