| Time | Status | Match | FT | H1 | Stats |
| 25/01/2020 02:00 |
(FT) | Waterhouse Dunbeholden |
3 1 |
2 1 |
MF | ME |
| 26/01/2020 21:00 |
(FT) | Portmore United Vere United |
5 0 |
2 0 |
MF | ME |
| 26/01/2020 21:00 |
(FT) | University Of West Indies Uwi Molynes United |
1 1 |
0 1 |
MF | ME |
| 26/01/2020 23:00 |
(FT) | Cavalier Harbour View |
1 1 |
1 1 |
MF | ME |
| 27/01/2020 02:00 |
(FT) | Arnett Gardens Tivoli Gardens |
1 1 |
1 0 |
MF | ME |
| 28/01/2020 02:00 |
(FT) | Mount Pleasant Humble Lions |
0 1 |
0 0 |
MF | ME |