2. Spieltag
19.09.2014 01:00 Waterhouse FC Waterhouse FC - Montego Bay United FC Montego Bay United FC 3:0
3. Spieltag
21.09.2014 22:30 Barbican FC - Cavalier FC Cavalier FC -:-
21.09.2014 22:30 Montego Bay United FC Montego Bay United FC - Boys' Town Boys' Town -:-
21.09.2014 23:00 Rivoli United Rivoli United - Sporting Central Sporting Central -:-
22.09.2014 01:00 Arnett Gardens Arnett Gardens - Tivoli Gardens Tivoli Gardens -:-
22.09.2014 01:30 Humble Lions Humble Lions - Waterhouse FC Waterhouse FC -:-
22.09.2014 01:30 Harbour View Harbour View - Reno United Reno United -:-
4. Spieltag
28.09.2014 Tivoli Gardens Tivoli Gardens - Rivoli United Rivoli United -:-
28.09.2014 Reno United Reno United - Arnett Gardens Arnett Gardens -:-
28.09.2014 Waterhouse FC Waterhouse FC - Harbour View Harbour View -:-
28.09.2014 Boys' Town Boys' Town - Humble Lions Humble Lions -:-
28.09.2014 Cavalier FC Cavalier FC - Montego Bay United FC Montego Bay United FC -:-
28.09.2014 Sporting Central Sporting Central - Barbican FC -:-