| Time | Status | Match | FT | H1 | Stats |
| 09/04/2023 20:00 |
(FT) | Dunbeholden[8] Montego Bay Utd[10] |
4 0 |
0 0 |
MF | ME |
| 09/04/2023 21:00 |
(FT) | Molynes United[9] Faulkland[14] |
2 2 |
1 1 |
MF | ME |
| 09/04/2023 22:15 |
(FT) | Mount Pleasant[5] Arnett Gardens[1] |
0 0 |
0 0 |
MF | ME |
| 09/04/2023 23:00 |
(FT) | Portmore United[7] Tivoli Gardens[11] |
2 1 |
2 0 |
MF | ME |
| 09/04/2023 23:15 |
(FT) | Waterhouse[6] Harbour View[3] |
0 2 |
0 1 |
MF | ME |
| 11/04/2023 00:00 |
(FT) | Cavalier[2] Humble Lions[4] |
1 0 |
1 0 |
MF | ME |
| 11/04/2023 02:30 |
(FT) | Chapelton[13] Vere United[12] |
0 4 |
0 3 |
MF | ME |