| Time | Status | Match | FT | H1 | Stats |
| 27/11/2019 20:00 |
(FT) | Molynes United Harbour View |
0 1 |
0 0 |
MF | ME |
| 27/11/2019 20:00 |
(FT) | Dunbeholden Humble Lions |
1 1 |
0 0 |
MF | ME |
| 27/11/2019 22:00 |
(FT) | Cavalier Vere United |
6 1 |
2 0 |
MF | ME |
| 28/11/2019 01:00 |
(FT) | Waterhouse Portmore United |
4 1 |
2 1 |
MF | ME |
| 28/11/2019 20:00 |
(FT) | Mount Pleasant Tivoli Gardens |
4 0 |
2 0 |
MF | ME |
| 28/11/2019 20:00 |
(FT) | University Of West Indies Uwi Arnett Gardens |
2 4 |
0 2 |
MF | ME |