5. Round
02/10/2016 21:30 Waterhouse FC Waterhouse FC - Maverley Hughenden FC -:-
02/10/2016 21:30 Montego Bay United FC Montego Bay United FC - Arnett Gardens Arnett Gardens -:-
02/10/2016 21:30 Portmore United Portmore United - Reno FC Reno FC -:-
02/10/2016 21:30 UWI Pelicans UWI Pelicans - Boys' Town Boys' Town -:-
02/10/2016 21:30 Jamalco FC - Tivoli Gardens Tivoli Gardens -:-
03/10/2016 01:00 Harbour View Harbour View - Humble Lions Humble Lions -:-
6. Round
09/10/2016 21:30 Tivoli Gardens Tivoli Gardens - Maverley Hughenden FC -:-
09/10/2016 21:30 Humble Lions Humble Lions - Montego Bay United FC Montego Bay United FC -:-
09/10/2016 21:30 Boys' Town Boys' Town - Jamalco FC -:-
09/10/2016 21:30 Reno FC Reno FC - UWI Pelicans UWI Pelicans -:-
10/10/2016 00:00 Arnett Gardens Arnett Gardens - Portmore United Portmore United -:-
10/10/2016 01:00 Harbour View Harbour View - Waterhouse FC Waterhouse FC -:-