| Time | Status | Match | FT | H1 | Stats |
| 30/04/2023 21:00 |
(FT) | Humble Lions[5] Mount Pleasant[4] |
1 1 |
1 0 |
MF | ME |
| 30/04/2023 21:00 |
(FT) | Tivoli Gardens[11] Montego Bay Utd[10] |
5 2 |
1 1 |
MF | ME |
| 30/04/2023 21:00 |
(FT) | Vere United[12] Faulkland[14] |
1 1 |
1 1 |
MF | ME |
| 30/04/2023 22:00 |
(FT) | Portmore United[7] Waterhouse[6] |
1 1 |
0 1 |
MF | ME |
| 30/04/2023 23:30 |
(FT) | Chapelton[13] Dunbeholden[8] |
1 7 |
1 2 |
MF | ME |
| 01/05/2023 23:00 |
(FT) | Cavalier Molynes United |
4 2 |
2 0 |
MF | ME |
| 02/05/2023 01:30 |
(FT) | Arnett Gardens[1] Harbour View[3] |
3 0 |
2 0 |
MF | ME |