| Time | Status | Match | FT | H1 | Stats |
| 14/01/2024 18:15 |
(FT) | Mount Pleasant[1] Treasure Beach[13] |
? ? |
? ? |
MF | ME |
| 14/01/2024 20:00 |
(FT) | Harbour View[9] Vere United[8] |
? ? |
? ? |
MF | ME |
| 14/01/2024 20:00 |
(FT) | Humble Lions[11] Dunbeholden[6] |
? ? |
? ? |
MF | ME |
| 15/01/2024 20:00 |
(FT) | Tivoli Gardens[4] Cavalier[3] |
? ? |
? ? |
MF | ME |
| 15/01/2024 20:15 |
(FT) | Lime Hall Academy[14] Portmore United[2] |
? ? |
? ? |
MF | ME |
| 15/01/2024 22:00 |
(FT) | Arnett Gardens[5] Molynes United[12] |
? ? |
? ? |
MF | ME |
| 16/01/2024 00:30 |
(FT) | Montego Bay Utd[10] Waterhouse[7] |
? ? |
? ? |
MF | ME |