| Time | Status | Match | FT | H1 | Stats |
| 29/09/2019 21:30 |
(FT) | Dunbeholden Molynes United |
0 1 |
0 1 |
MF | ME |
| 29/09/2019 21:30 |
(FT) | Portmore United Humble Lions |
2 0 |
1 0 |
MF | ME |
| 29/09/2019 21:30 |
(FT) | Vere United Harbour View |
1 1 |
1 0 |
MF | ME |
| 29/09/2019 22:00 |
(FT) | Mount Pleasant Arnett Gardens |
2 2 |
1 1 |
MF | ME |
| 01/10/2019 02:30 |
(FT) | Cavalier University Of West Indies Uwi |
4 0 |
1 0 |
MF | ME |
| 11/10/2019 01:45 |
(FT) | Waterhouse Tivoli Gardens |
2 1 |
0 1 |
MF | ME |