| Time | Status | Match | FT | H1 | Stats |
| 11/12/2019 20:00 |
(FT) | Tivoli Gardens Molynes United |
2 0 |
0 0 |
MF | ME |
| 12/12/2019 01:00 |
(FT) | Harbour View Vere United |
2 0 |
1 0 |
MF | ME |
| 12/12/2019 01:00 |
(FT) | Arnett Gardens Waterhouse |
1 1 |
0 0 |
MF | ME |
| 12/12/2019 20:00 |
(FT) | Portmore United Cavalier |
2 1 |
1 0 |
MF | ME |
| 12/12/2019 22:00 |
(FT) | Humble Lions University Of West Indies Uwi |
2 0 |
2 0 |
MF | ME |
| 13/12/2019 00:00 |
(FT) | Mount Pleasant Dunbeholden |
2 1 |
1 0 |
MF | ME |