2. Round
14/09/2014 21:30 Boys' Town Boys' Town - Barbican FC 1:1
14/09/2014 21:30 Reno United Reno United - Humble Lions Humble Lions 3:2
14/09/2014 21:30 Tivoli Gardens Tivoli Gardens - Harbour View Harbour View 0:0
14/09/2014 23:00 Cavalier FC Cavalier FC - Sporting Central Sporting Central 1:0
16/09/2014 03:00 Arnett Gardens Arnett Gardens - Rivoli United Rivoli United 2:2
19/09/2014 00:00 Waterhouse FC Waterhouse FC - Montego Bay United FC Montego Bay United FC -:-
3. Round
21/09/2014 Rivoli United Rivoli United - Sporting Central Sporting Central -:-
21/09/2014 Barbican FC - Cavalier FC Cavalier FC -:-
21/09/2014 Montego Bay United FC Montego Bay United FC - Boys' Town Boys' Town -:-
21/09/2014 Humble Lions Humble Lions - Waterhouse FC Waterhouse FC -:-
21/09/2014 Harbour View Harbour View - Reno United Reno United -:-
21/09/2014 Arnett Gardens Arnett Gardens - Tivoli Gardens Tivoli Gardens -:-