| Time | Status | Match | FT | H1 | Stats |
| 20/10/2019 21:30 |
(FT) | Humble Lions Harbour View |
0 0 |
0 0 |
MF | ME |
| 20/10/2019 21:30 |
(FT) | Molynes United Cavalier |
1 3 |
0 2 |
MF | ME |
| 20/10/2019 21:30 |
(FT) | Tivoli Gardens Dunbeholden |
1 0 |
0 0 |
MF | ME |
| 20/10/2019 21:30 |
(FT) | University Of West Indies Uwi Vere United |
1 1 |
1 1 |
MF | ME |
| 20/10/2019 22:00 |
(FT) | Mount Pleasant Waterhouse |
3 1 |
2 0 |
MF | ME |
| 22/10/2019 02:30 |
(FT) | Arnett Gardens Portmore United |
1 0 |
0 0 |
MF | ME |