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| 22.10.2019 | ||||
| 03:30 | D1 Regular Season | Arnett Gardens | 1-0 | Portmore United |
| 20.10.2019 | ||||
| 23:00 | D1 Regular Season | Mount Pleasant | 3-1 | Waterhouse FC |
| 22:30 | D1 Regular Season | Humble Lions | 0-0 | Harbour View |
| 22:30 | D1 Regular Season | Molynes United | 1-3 | Cavalier FC |
| 22:30 | D1 Regular Season | Tivoli Gardens | 1-0 | Dunbeholden FC |
| 22:30 | D1 Regular Season | UWI FC | 1-1 | Vere United |
| 15.10.2019 | ||||
| 03:30 | D1 Regular Season | Cavalier FC | 2-2 | Mount Pleasant |
| 14.10.2019 | ||||
| 02:00 | D1 Regular Season | Harbour View | 0-0 | Molynes United |
| 02:00 | D1 Regular Season | Waterhouse FC | 3-1 | Arnett Gardens |
| 13.10.2019 | ||||
| 22:30 | D1 Regular Season | Dunbeholden FC | 0-0 | Humble Lions |
| 22:30 | D1 Regular Season | Portmore United | 2-1 | UWI FC |
| 22:30 | D1 Regular Season | Vere United | 1-1 | Tivoli Gardens |
| 27.10.2019 | |||||
| 21:00 | D1 Regular Season | Dunbeholden FC | - | UWI FC | |
| 21:00 | D1 Regular Season | Harbour View | - | Tivoli Gardens | |
| 21:00 | D1 Regular Season | Humble Lions | - | Molynes United | |
| 21:00 | D1 Regular Season | Portmore United | - | Mount Pleasant | |
| 21:00 | D1 Regular Season | Vere United | - | Arnett Gardens | |
| 29.10.2019 | |||||
| 02:30 | D1 Regular Season | Waterhouse FC | - | Cavalier FC | |
| 03.11.2019 | |||||
| 22:30 | D1 Regular Season | Arnett Gardens | - | Dunbeholden FC | |
| 22:30 | D1 Regular Season | Cavalier FC | - | Portmore United | |
| 22:30 | D1 Regular Season | Molynes United | - | Waterhouse FC | |
| 22:30 | D1 Regular Season | Mount Pleasant | - | Vere United | |
| 22:30 | D1 Regular Season | Tivoli Gardens | - | Humble Lions | |
| 22:30 | D1 Regular Season | UWI FC | - | Harbour View | |