| Time | Status | Match | FT | H1 | Stats |
| 29/12/2019 20:00 |
(FT) | Molynes United Dunbeholden |
2 3 |
1 2 |
MF | ME |
| 29/12/2019 20:00 |
(FT) | Vere United Tivoli Gardens |
1 1 |
1 1 |
MF | ME |
| 29/12/2019 22:00 |
(FT) | Humble Lions Arnett Gardens |
1 2 |
0 1 |
MF | ME |
| 30/12/2019 00:00 |
(FT) | Harbour View Portmore United |
1 0 |
0 0 |
MF | ME |
| 30/12/2019 01:00 |
(FT) | Cavalier Waterhouse |
1 0 |
0 0 |
MF | ME |
| 31/12/2019 01:00 |
(FT) | University Of West Indies Uwi Mount Pleasant |
0 3 |
0 0 |
MF | ME |