| Time | Status | Match | FT | H1 | Stats |
| 13/10/2019 22:30 |
(FT) | Dunbeholden Humble Lions |
0 0 |
0 0 |
MF | ME |
| 13/10/2019 22:30 |
(FT) | Portmore United University Of West Indies Uwi |
2 1 |
2 1 |
MF | ME |
| 13/10/2019 22:30 |
(FT) | Vere United Tivoli Gardens |
1 1 |
1 0 |
MF | ME |
| 14/10/2019 02:00 |
(FT) | Harbour View Molynes United |
0 0 |
0 0 |
MF | ME |
| 14/10/2019 02:00 |
(FT) | Waterhouse Arnett Gardens |
3 1 |
1 0 |
MF | ME |
| 15/10/2019 03:30 |
(FT) | Cavalier Mount Pleasant |
2 2 |
0 0 |
MF | ME |