| Time | Status | Match | FT | H1 | Stats |
| 19/01/2020 20:00 |
(FT) | Dunbeholden Cavalier |
1 0 |
0 0 |
MF | ME |
| 19/01/2020 20:00 |
(FT) | Molynes United Portmore United |
0 2 |
0 2 |
MF | ME |
| 19/01/2020 20:00 |
(FT) | Tivoli Gardens University Of West Indies Uwi |
1 0 |
0 0 |
MF | ME |
| 19/01/2020 20:00 |
(FT) | Vere United Waterhouse |
0 1 |
0 0 |
MF | ME |
| 19/01/2020 22:00 |
(FT) | Humble Lions Arnett Gardens |
3 1 |
1 0 |
MF | ME |
| 21/01/2020 01:00 |
(FT) | Harbour View Mount Pleasant |
1 1 |
1 0 |
MF | ME |