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| 12.07.2021 | ||||
| 22:30 | D1 Regular Season | Arnett Gardens | 2-1 | Humble Lions |
| 11.07.2021 | ||||
| 22:30 | D1 Regular Season | Waterhouse FC | 0-0 | Vere United |
| 20:00 | D1 Regular Season | Cavalier FC | 0-1 | Dunbeholden FC |
| 10.07.2021 | ||||
| 22:30 | D1 Regular Season | Mount Pleasant | 0-2 | Harbour View |
| 20:00 | D1 Regular Season | Portmore United | 1-0 | Molynes United |
| 06.07.2021 | ||||
| 22:30 | D1 Regular Season | Vere United | 1-0 | Portmore United |
| 20:00 | D1 Regular Season | Tivoli Gardens | 1-0 | Arnett Gardens |
| 05.07.2021 | ||||
| 22:30 | D1 Regular Season | Harbour View | 1-1 | Cavalier FC |
| 03.07.2021 | ||||
| 22:30 | D1 Regular Season | Dunbeholden FC | 0-2 | Waterhouse FC |
| 20:00 | D1 Regular Season | Humble Lions | 0-1 | Mount Pleasant |
| 28.06.2021 | ||||
| 22:30 | D1 Regular Season | Waterhouse FC | 1-1 | Harbour View |
| 20:00 | D1 Regular Season | Vere United | 0-0 | Molynes United |
| 27.06.2021 | ||||
| 18:00 | D1 Regular Season | Portmore United | 2-0 | Dunbeholden FC |
| 26.06.2021 | ||||
| 22:40 | D1 Regular Season | Cavalier FC | 2-0 | Humble Lions |
| 20:15 | D1 Regular Season | Mount Pleasant | 0-0 | Tivoli Gardens |