3. Round
15/09/2019 21:30 Portmore United Portmore United - Dunbeholden FC Dunbeholden FC 0:1
15/09/2019 21:30 Vere United Vere United - Molynes United 0:1
15/09/2019 22:00 Mount Pleasant Academy Mount Pleasant Academy - Tivoli Gardens Tivoli Gardens 1:0
15/09/2019 23:00 Cavalier FC Cavalier FC - Humble Lions Humble Lions 1:1
16/09/2019 01:00 Waterhouse FC Waterhouse FC - Harbour View Harbour View 7:0
17/09/2019 02:30 Arnett Gardens Arnett Gardens - UWI Pelicans UWI Pelicans 0:0
4. Round
22/09/2019 Dunbeholden FC Dunbeholden FC - Vere United Vere United -:-
22/09/2019 Harbour View Harbour View - Portmore United Portmore United -:-
22/09/2019 Humble Lions Humble Lions - Waterhouse FC Waterhouse FC -:-
22/09/2019 Molynes United - Arnett Gardens Arnett Gardens -:-
22/09/2019 Tivoli Gardens Tivoli Gardens - Cavalier FC Cavalier FC -:-
22/09/2019 UWI Pelicans UWI Pelicans - Mount Pleasant Academy Mount Pleasant Academy -:-