| Time | Status | Match | FT | H1 | Stats |
| 12/03/2023 20:00 |
(FT) | Portmore United[8] Mount Pleasant[2] |
? ? |
? ? |
MF | ME |
| 12/03/2023 20:00 |
(FT) | Tivoli Gardens[10] Faulkland[14] |
0 0 |
0 0 |
MF | ME |
| 12/03/2023 20:00 |
(FT) | Cavalier[3] Dunbeholden[6] |
3 1 |
2 1 |
MF | ME |
| 12/03/2023 21:00 |
(FT) | Chapelton[13] Waterhouse[7] |
2 3 |
1 0 |
MF | ME |
| 12/03/2023 22:30 |
(FT) | Arnett Gardens[1] Montego Bay Utd[9] |
1 1 |
1 0 |
MF | ME |
| 13/03/2023 22:00 |
(FT) | Vere United[12] Molynes United[11] |
0 4 |
0 2 |
MF | ME |
| 14/03/2023 00:30 |
(FT) | Harbour View[4] Humble Lions[5] |
1 0 |
0 0 |
MF | ME |
| 06/04/2023 22:00 |
(FT) | Portmore United[7] Mount Pleasant[5] |
0 0 |
0 0 |
MF | ME |