| Time | Status | Match | FT | H1 | Stats |
| 01/09/2019 22:30 |
(FT) | University Of West Indies Uwi Tivoli Gardens |
4 0 |
1 0 |
MF | ME |
| 01/09/2019 23:00 |
(FT) | Mount Pleasant Harbour View |
1 2 |
0 0 |
MF | ME |
| 02/09/2019 00:00 |
(FT) | Cavalier Dunbeholden |
3 1 |
1 0 |
MF | ME |
| 02/09/2019 02:00 |
(FT) | Arnett Gardens Humble Lions |
1 3 |
1 1 |
MF | ME |
| 03/09/2019 03:45 |
(FT) | Portmore United Molynes United |
0 3 |
0 2 |
MF | ME |
| 12/09/2019 22:00 |
(FT) | Waterhouse Vere United |
2 0 |
1 0 |
MF | ME |