National Premier League
 
FT
UWI
Portmore United
1
2
 
FT
Portmore United
Vere United
3
1
 
FT
Harbour View
Portmore United
1
0
 
FT
Portmore United
Humble Lions
0
2
 
FT
Portmore United
Arnett Gardens
2
0
 
FT
Molynes United
Portmore United
0
2
 
FT
Portmore United
Vere United
5
0
 
FT
Dunbeholden
Portmore United
1
4
 CONCACAF Champions League
 
FT
Portmore United
Cruz Azul
1
2
 
FT
Cruz Azul
Portmore United
4
0
 National Premier League
 
FT
Portmore United
Tivoli Gardens
0
1
 
FT
Portmore United
Harbour View
0
0
 
FT
UWI
Portmore United
1
3
Postp.
Humble Lions
Portmore United
Postp.
Portmore United
Arnett Gardens
Postp.
Mount Pleasant Academy
Portmore United
Postp.
Portmore United
Cavalier
Postp.
Waterhouse
Portmore United
 
Portmore United
Cavalier
Postp.
Waterhouse
Portmore United