30. Round
20/04/2014 21:30 August Town FC August Town FC - Sporting Central Sporting Central 0:1
20/04/2014 21:30 Boys' Town Boys' Town - Waterhouse FC Waterhouse FC 0:1
20/04/2014 22:00 Tivoli Gardens Tivoli Gardens - Portmore United Portmore United 1:0
20/04/2014 22:30 Cavalier FC Cavalier FC - Rivoli United 0:2
21/04/2014 00:30 Harbour View Harbour View - Humble Lions Humble Lions 2:2
22/04/2014 02:30 Montego Bay United FC Montego Bay United FC - Arnett Gardens Arnett Gardens 0:1
31. Round
25/04/2014 Humble Lions Humble Lions - Tivoli Gardens Tivoli Gardens -:-
25/04/2014 Rivoli United - Portmore United Portmore United -:-
25/04/2014 Cavalier FC Cavalier FC - Boys' Town Boys' Town -:-
25/04/2014 Waterhouse FC Waterhouse FC - Harbour View Harbour View -:-
25/04/2014 Arnett Gardens Arnett Gardens - Sporting Central Sporting Central -:-
25/04/2014 Montego Bay United FC Montego Bay United FC - August Town FC August Town FC -:-
32. Round
28/04/2014 August Town FC August Town FC - Arnett Gardens Arnett Gardens -:-
28/04/2014 Boys' Town Boys' Town - Humble Lions Humble Lions -:-
28/04/2014 Sporting Central Sporting Central - Rivoli United -:-
28/04/2014 Tivoli Gardens Tivoli Gardens - Cavalier FC Cavalier FC -:-
28/04/2014 Harbour View Harbour View - Montego Bay United FC Montego Bay United FC -:-
28/04/2014 Portmore United Portmore United - Waterhouse FC Waterhouse FC -:-