23. Round
20/01/2019 20:00 Mount Pleasant Academy Mount Pleasant Academy - Portmore United Portmore United 1:1
20/01/2019 20:00 Humble Lions Humble Lions - Arnett Gardens Arnett Gardens 2:1
20/01/2019 20:00 Dunbeholden FC Dunbeholden FC - Waterhouse FC Waterhouse FC 0:0
20/01/2019 22:00 Cavalier FC Cavalier FC - Reno FC Reno FC 0:0
21/01/2019 00:00 Tivoli Gardens Tivoli Gardens - Montego Bay United FC Montego Bay United FC 2:1
22/01/2019 01:35 Harbour View Harbour View - UWI Pelicans UWI Pelicans -:-
24. Round
27/01/2019 20:00 Montego Bay United FC Montego Bay United FC - Dunbeholden FC Dunbeholden FC -:-
27/01/2019 20:00 UWI Pelicans UWI Pelicans - Humble Lions Humble Lions -:-
27/01/2019 20:00 Reno FC Reno FC - Tivoli Gardens Tivoli Gardens -:-
27/01/2019 20:00 Portmore United Portmore United - Harbour View Harbour View -:-
28/01/2019 00:00 Waterhouse FC Waterhouse FC - Mount Pleasant Academy Mount Pleasant Academy -:-
29/01/2019 01:35 Arnett Gardens Arnett Gardens - Cavalier FC Cavalier FC -:-