| Time | Status | Match | FT | H1 | Stats |
| 22/12/2019 21:00 |
(FT) | Tivoli Gardens University Of West Indies Uwi |
2 2 |
0 1 |
MF | ME |
| 22/12/2019 21:00 |
(FT) | Portmore United Vere United |
3 1 |
2 0 |
MF | ME |
| 22/12/2019 23:00 |
(FT) | Humble Lions Harbour View |
1 0 |
1 0 |
MF | ME |
| 23/12/2019 01:00 |
(FT) | Mount Pleasant Cavalier |
0 1 |
0 0 |
MF | ME |
| 23/12/2019 02:00 |
(FT) | Arnett Gardens Dunbeholden |
0 3 |
0 3 |
MF | ME |
| 24/12/2019 02:00 |
(FT) | Waterhouse Molynes United |
1 2 |
0 1 |
MF | ME |