| Time | Status | Match | FT | H1 | Stats |
| 19/03/2023 20:00 |
(FT) | Harbour View[4] Tivoli Gardens[11] |
2 2 |
1 1 |
MF | ME |
| 19/03/2023 20:00 |
(FT) | Humble Lions[5] Arnett Gardens[1] |
1 1 |
1 0 |
MF | ME |
| 19/03/2023 20:00 |
(FT) | Montego Bay Utd[9] Vere United[12] |
3 3 |
1 1 |
MF | ME |
| 19/03/2023 21:00 |
(FT) | Waterhouse[6] Mount Pleasant[3] |
2 0 |
1 0 |
MF | ME |
| 19/03/2023 22:30 |
(FT) | Dunbeholden[7] Portmore United[8] |
1 3 |
0 0 |
MF | ME |
| 20/03/2023 22:00 |
(FT) | Molynes United[10] Chapelton[13] |
3 1 |
3 0 |
MF | ME |
| 21/03/2023 00:30 |
(FT) | Faulkland[14] Cavalier[2] |
2 2 |
1 0 |
MF | ME |