| Time | Status | Match | FT | H1 | Stats |
| 08/01/2023 18:00 |
(FT) | Faulkland Molynes United |
2 2 |
2 0 |
MF | ME |
| 08/01/2023 20:00 |
(FT) | Tivoli Gardens Portmore United |
0 0 |
0 0 |
MF | ME |
| 08/01/2023 20:00 |
(FT) | Vere United Chapelton |
0 0 |
0 0 |
MF | ME |
| 08/01/2023 22:30 |
(FT) | Harbour View Waterhouse |
0 4 |
0 2 |
MF | ME |
| 09/01/2023 00:30 |
(FT) | Montego Bay Utd Dunbeholden |
0 2 |
0 0 |
MF | ME |
| 09/01/2023 22:00 |
(FT) | Humble Lions Cavalier |
1 2 |
1 0 |
MF | ME |
| 10/01/2023 00:30 |
(FT) | Arnett Gardens Mount Pleasant |
3 2 |
2 0 |
MF | ME |