Halbfinale
08.05.2014 02:00 Harbour View Harbour View - Montego Bay United FC Montego Bay United FC 2:2
09.05.2014 02:00 Waterhouse FC Waterhouse FC - Arnett Gardens Arnett Gardens 3:3
11.05.2014 22:00 Montego Bay United FC Montego Bay United FC - Harbour View Harbour View 1:0
13.05.2014 03:30 Arnett Gardens Arnett Gardens - Waterhouse FC Waterhouse FC 1:2
Finale
20.05.2014 03:30 Montego Bay United FC Montego Bay United FC - Waterhouse FC Waterhouse FC 5:2