| Time | Status | Match | FT | H1 | Stats |
| 15/12/2019 20:00 |
(FT) | Molynes United Mount Pleasant |
1 4 |
0 2 |
MF | ME |
| 15/12/2019 20:00 |
(FT) | Dunbeholden Waterhouse |
1 1 |
0 0 |
MF | ME |
| 15/12/2019 20:00 |
(FT) | University Of West Indies Uwi Portmore United |
1 2 |
1 0 |
MF | ME |
| 15/12/2019 20:00 |
(FT) | Vere United Humble Lions |
1 1 |
1 1 |
MF | ME |
| 16/12/2019 00:00 |
(FT) | Harbour View Arnett Gardens |
1 2 |
0 2 |
MF | ME |
| 17/12/2019 01:00 |
(FT) | Cavalier Tivoli Gardens |
2 3 |
0 3 |
MF | ME |