| Time | Status | Match | FT | H1 | Stats |
| 05/01/2020 21:00 |
(FT) | Dunbeholden Cavalier |
2 0 |
1 0 |
MF | ME |
| 05/01/2020 21:00 |
(FT) | Tivoli Gardens Harbour View |
3 0 |
2 0 |
MF | ME |
| 05/01/2020 21:00 |
(FT) | Portmore United Humble Lions |
0 2 |
0 1 |
MF | ME |
| 06/01/2020 01:00 |
(FT) | Mount Pleasant Vere United |
2 0 |
1 0 |
MF | ME |
| 06/01/2020 01:00 |
(FT) | Waterhouse University Of West Indies Uwi |
2 2 |
1 0 |
MF | ME |
| 07/01/2020 02:00 |
(FT) | Arnett Gardens Molynes United |
2 2 |
1 1 |
MF | ME |