33. Round
04/05/2014 23:00 Waterhouse FC Waterhouse FC - Sporting Central Sporting Central 5:0
05/05/2014 00:00 Arnett Gardens Arnett Gardens - Boys' Town Boys' Town 1:2
05/05/2014 21:30 Rivoli United Rivoli United - Tivoli Gardens Tivoli Gardens 1:2
05/05/2014 21:30 August Town FC August Town FC - Harbour View Harbour View 0:4
05/05/2014 21:30 Humble Lions Humble Lions - Portmore United Portmore United 3:1
05/05/2014 22:30 Cavalier FC Cavalier FC - Montego Bay United FC Montego Bay United FC 0:0