| Time | Status | Match | FT | H1 | Stats |
| 03/11/2019 20:00 |
(FT) | Molynes United Waterhouse |
1 2 |
0 1 |
MF | ME |
| 03/11/2019 20:00 |
(FT) | Tivoli Gardens Humble Lions |
1 2 |
0 1 |
MF | ME |
| 03/11/2019 20:00 |
(FT) | University Of West Indies Uwi Harbour View |
2 2 |
1 1 |
MF | ME |
| 03/11/2019 20:00 |
(FT) | Mount Pleasant Vere United |
2 1 |
1 0 |
MF | ME |
| 03/11/2019 22:00 |
(FT) | Cavalier Portmore United |
0 0 |
0 0 |
MF | ME |
| 05/11/2019 01:00 |
(FT) | Arnett Gardens Dunbeholden |
2 2 |
0 0 |
MF | ME |