24. Round
25/01/2020 01:00 Waterhouse FC Waterhouse FC - Dunbeholden FC Dunbeholden FC 3:1
26/01/2020 20:30 Portmore United Portmore United - Vere United Vere United 5:0
26/01/2020 20:30 UWI Pelicans UWI Pelicans - Molynes United 1:1
26/01/2020 22:00 Cavalier FC Cavalier FC - Harbour View Harbour View 1:1
27/01/2020 01:00 Arnett Gardens Arnett Gardens - Tivoli Gardens Tivoli Gardens 1:1
28/01/2020 01:00 Mount Pleasant Academy Mount Pleasant Academy - Humble Lions Humble Lions -:-
25. Round
30/01/2020 20:00 Dunbeholden FC Dunbeholden FC - Portmore United Portmore United -:-
30/01/2020 20:00 Molynes United - Vere United Vere United -:-
30/01/2020 20:00 Tivoli Gardens Tivoli Gardens - Mount Pleasant Academy Mount Pleasant Academy -:-
30/01/2020 20:00 UWI Pelicans UWI Pelicans - Arnett Gardens Arnett Gardens -:-
30/01/2020 22:00 Humble Lions Humble Lions - Cavalier FC Cavalier FC -:-
13/02/2020 00:00 Harbour View Harbour View - Waterhouse FC Waterhouse FC -:-