| Time | Status | Match | FT | H1 | Stats |
| 23/04/2023 20:00 |
(FT) | Molynes United[9] Tivoli Gardens[11] |
4 3 |
2 2 |
MF | ME |
| 23/04/2023 21:00 |
(FT) | Faulkland[14] Arnett Gardens[2] |
0 2 |
0 2 |
MF | ME |
| 23/04/2023 22:00 |
(FT) | Portmore United[7] Humble Lions[5] |
1 1 |
0 1 |
MF | ME |
| 23/04/2023 22:30 |
(FT) | Waterhouse[6] Cavalier[1] |
1 0 |
1 0 |
MF | ME |
| 23/04/2023 23:30 |
(FT) | Montego Bay Utd[10] Harbour View[3] |
0 1 |
0 1 |
MF | ME |
| 24/04/2023 23:00 |
(FT) | Dunbeholden[8] Vere United[12] |
3 1 |
0 0 |
MF | ME |
| 25/04/2023 01:30 |
(FT) | Mount Pleasant[4] Chapelton[13] |
7 0 |
2 0 |
MF | ME |