| Time | Status | Match | FT | H1 | Stats |
| 16/04/2023 22:00 |
(FT) | Humble Lions[5] Chapelton[13] |
4 0 |
0 0 |
MF | ME |
| 16/04/2023 22:00 |
(FT) | Vere United[11] Mount Pleasant[4] |
0 5 |
0 2 |
MF | ME |
| 16/04/2023 22:00 |
(FT) | Cavalier[1] Portmore United[6] |
2 0 |
1 0 |
MF | ME |
| 16/04/2023 22:00 |
(FT) | Montego Bay Utd[10] Faulkland[14] |
2 1 |
2 0 |
MF | ME |
| 17/04/2023 00:30 |
(FT) | Harbour View Molynes United |
1 1 |
0 0 |
MF | ME |
| 18/04/2023 00:00 |
(FT) | Arnett Gardens[2] Dunbeholden[8] |
1 0 |
0 0 |
MF | ME |
| 18/04/2023 02:30 |
(FT) | Tivoli Gardens[12] Waterhouse[7] |
0 1 |
0 1 |
MF | ME |