| Time | Status | Match | FT | H1 | Stats |
| 22/01/2023 21:00 |
(FT) | Harbour View Montego Bay Utd |
1 0 |
1 0 |
MF | ME |
| 22/01/2023 21:00 |
(FT) | Tivoli Gardens Molynes United |
2 1 |
1 0 |
MF | ME |
| 22/01/2023 21:10 |
(FT) | Humble Lions Portmore United |
1 0 |
0 0 |
MF | ME |
| 22/01/2023 21:15 |
(FT) | Chapelton Mount Pleasant |
0 3 |
0 0 |
MF | ME |
| 22/01/2023 23:30 |
(FT) | Cavalier Waterhouse |
0 1 |
0 0 |
MF | ME |
| 23/01/2023 23:00 |
(FT) | Vere United Dunbeholden |
0 1 |
0 0 |
MF | ME |
| 24/01/2023 01:30 |
(FT) | Arnett Gardens Faulkland |
0 0 |
0 0 |
MF | ME |