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| 14.01.2020 | ||||
| 02:00 | D1 Regular Season | Harbour View | 1-0 | Mount Pleasant |
| 12.01.2020 | ||||
| 23:00 | D1 Regular Season | Cavalier FC | 4-0 | Molynes United |
| 21:00 | D1 Regular Season | Humble Lions | 0-3 | Tivoli Gardens |
| 21:00 | D1 Regular Season | Portmore United | 2-0 | Arnett Gardens |
| 21:00 | D1 Regular Season | UWI FC | 0-0 | Dunbeholden FC |
| 21:00 | D1 Regular Season | Vere United | 0-0 | Waterhouse FC |
| 07.01.2020 | ||||
| 02:00 | D1 Regular Season | Arnett Gardens | 2-2 | Molynes United |
| 06.01.2020 | ||||
| 01:00 | D1 Regular Season | Mount Pleasant | 2-0 | Vere United |
| 01:00 | D1 Regular Season | Waterhouse FC | 2-2 | UWI FC |
| 05.01.2020 | ||||
| 21:00 | D1 Regular Season | Dunbeholden FC | 2-0 | Cavalier FC |
| 21:00 | D1 Regular Season | Portmore United | 0-2 | Humble Lions |
| 21:00 | D1 Regular Season | Tivoli Gardens | 3-0 | Harbour View |
| 19.01.2020 | |||||
| 21:00 | D1 Regular Season | Dunbeholden FC | - | Cavalier FC | |
| 21:00 | D1 Regular Season | Molynes United | - | Portmore United | |
| 21:00 | D1 Regular Season | Tivoli Gardens | - | UWI FC | |
| 21:00 | D1 Regular Season | Vere United | - | Waterhouse FC | |
| 23:00 | D1 Regular Season | Humble Lions | - | Arnett Gardens | |
| 21.01.2020 | |||||
| 02:00 | D1 Regular Season | Harbour View | - | Mount Pleasant | |
| 26.01.2020 | |||||
| 21:30 | D1 Regular Season | Portmore United | - | Vere United | |
| 21:30 | D1 Regular Season | UWI FC | - | Molynes United | |
| 22:00 | D1 Regular Season | Mount Pleasant | - | Humble Lions | |
| 23:00 | D1 Regular Season | Cavalier FC | - | Harbour View | |
| 27.01.2020 | |||||
| 01:00 | D1 Regular Season | Arnett Gardens | - | Tivoli Gardens | |
| 01:00 | D1 Regular Season | Waterhouse FC | - | Dunbeholden FC | |