4. Spieltag
28.09.2014 Reno United Reno United - Arnett Gardens Arnett Gardens verl.
28.09.2014 Sporting Central Sporting Central - Barbican FC verl.
28.09.2014 22:30 Tivoli Gardens Tivoli Gardens - Rivoli United Rivoli United 2:3
29.09.2014 Waterhouse FC Waterhouse FC - Harbour View Harbour View verl.
29.09.2014 00:00 Cavalier FC Cavalier FC - Montego Bay United FC Montego Bay United FC 1:0
30.09.2014 04:15 Boys' Town Boys' Town - Humble Lions Humble Lions 2:0
5. Spieltag
05.10.2014 Rivoli United Rivoli United - Barbican FC -:-
05.10.2014 Montego Bay United FC Montego Bay United FC - Sporting Central Sporting Central -:-
05.10.2014 Humble Lions Humble Lions - Cavalier FC Cavalier FC -:-
05.10.2014 Harbour View Harbour View - Boys' Town Boys' Town -:-
05.10.2014 Arnett Gardens Arnett Gardens - Waterhouse FC Waterhouse FC -:-
05.10.2014 Tivoli Gardens Tivoli Gardens - Reno United Reno United -:-