4. Spieltag
29.10.2014 21:00 Sporting Central Sporting Central - Barbican FC 3:3
30.10.2014 Waterhouse FC Waterhouse FC - Harbour View Harbour View 1:2
9. Spieltag
09.11.2014 21:00 Tivoli Gardens Tivoli Gardens - Sporting Central Sporting Central -:-
09.11.2014 21:00 Reno United Reno United - Cavalier FC Cavalier FC -:-
10.11.2014 00:00 Arnett Gardens Arnett Gardens - Barbican FC -:-
10.11.2014 00:00 Waterhouse FC Waterhouse FC - Boys' Town Boys' Town -:-
10.11.2014 00:30 Humble Lions Humble Lions - Rivoli United Rivoli United -:-
10.11.2014 00:30 Harbour View Harbour View - Montego Bay United FC Montego Bay United FC -:-
10. Spieltag
23.11.2014 Rivoli United Rivoli United - Boys' Town Boys' Town -:-
23.11.2014 Cavalier FC Cavalier FC - Waterhouse FC Waterhouse FC -:-
23.11.2014 Sporting Central Sporting Central - Reno United Reno United -:-
23.11.2014 Barbican FC - Tivoli Gardens Tivoli Gardens -:-
23.11.2014 Montego Bay United FC Montego Bay United FC - Arnett Gardens Arnett Gardens -:-
23.11.2014 Humble Lions Humble Lions - Harbour View Harbour View -:-