4. Round
23/10/2014 21:00 Reno United Reno United - Arnett Gardens Arnett Gardens 2:1
8. Round
26/10/2014 20:00 Rivoli United Rivoli United - Waterhouse FC Waterhouse FC -:-
26/10/2014 20:00 Boys' Town Boys' Town - Reno United Reno United -:-
26/10/2014 20:00 Sporting Central Sporting Central - Arnett Gardens Arnett Gardens -:-
26/10/2014 20:00 Barbican FC - Harbour View Harbour View -:-
26/10/2014 20:00 Montego Bay United FC Montego Bay United FC - Humble Lions Humble Lions -:-
28/10/2014 02:00 Cavalier FC Cavalier FC - Tivoli Gardens Tivoli Gardens -:-
9. Round
09/11/2014 Humble Lions Humble Lions - Rivoli United Rivoli United -:-
09/11/2014 Harbour View Harbour View - Montego Bay United FC Montego Bay United FC -:-
09/11/2014 Arnett Gardens Arnett Gardens - Barbican FC -:-
09/11/2014 Tivoli Gardens Tivoli Gardens - Sporting Central Sporting Central -:-
09/11/2014 Reno United Reno United - Cavalier FC Cavalier FC -:-
09/11/2014 Waterhouse FC Waterhouse FC - Boys' Town Boys' Town -:-