| Time | Status | Match | FT | H1 | Stats |
| 30/01/2020 21:00 |
(FT) | Dunbeholden Portmore United |
1 4 |
0 2 |
MF | ME |
| 30/01/2020 21:00 |
(FT) | Molynes United Vere United |
1 1 |
1 1 |
MF | ME |
| 30/01/2020 21:00 |
(FT) | Tivoli Gardens Mount Pleasant |
0 2 |
0 1 |
MF | ME |
| 30/01/2020 21:00 |
(FT) | University Of West Indies Uwi Arnett Gardens |
1 3 |
0 1 |
MF | ME |
| 30/01/2020 23:00 |
(FT) | Humble Lions Cavalier |
2 1 |
1 0 |
MF | ME |
| 13/02/2020 01:00 |
(FT) | Harbour View Waterhouse |
1 1 |
1 0 |
MF | ME |