| Time | Status | Match | FT | H1 | Stats |
| 27/10/2019 20:30 |
(FT) | Dunbeholden University Of West Indies Uwi |
1 0 |
0 0 |
MF | ME |
| 27/10/2019 20:30 |
(FT) | Humble Lions Molynes United |
2 1 |
0 0 |
MF | ME |
| 27/10/2019 20:30 |
(FT) | Vere United Arnett Gardens |
1 1 |
0 0 |
MF | ME |
| 28/10/2019 00:00 |
(FT) | Harbour View Tivoli Gardens |
1 0 |
0 0 |
MF | ME |
| 29/10/2019 01:00 |
(FT) | Waterhouse Cavalier |
0 0 |
0 0 |
MF | ME |
| 30/10/2019 20:00 |
(FT) | Portmore United Mount Pleasant |
0 2 |
0 1 |
MF | ME |