National Premier League
 
Final
Harbour View
Mount Pleasant Academy
1
0
 
Final
Mount Pleasant Academy
Harbour View
4
1
 
Final
Mount Pleasant Academy
Portmore United
1
1
 
Final
Tivoli Gardens
Mount Pleasant Academy
1
1
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 Copa de Campeones de la Concacaf
 
Final
LA Galaxy
Mount Pleasant Academy
Fox Sports 2, fuboTV, TUDN USA, TUDN.com, Foxsports.com
3
0
 National Premier League
 
Final
Mount Pleasant Academy
Molynes United
2
0
 Copa de Campeones de la Concacaf
 
Final
Mount Pleasant Academy
LA Galaxy
Fox Sports 1, fuboTV, TUDN USA, TUDN.com, Foxsports.com
0
3
 National Premier League
 
Final
Mount Pleasant Academy
Portmore United
4
1
 
Final
Mount Pleasant Academy
Police
4
0
 
Final
Arnett Gardens
Mount Pleasant Academy
1
1
 
Final
Police
Mount Pleasant Academy
1
0
 
Final
Mount Pleasant Academy
Racing United
0
0
 
Final
Cavalier
Mount Pleasant Academy
1
3
 
Final
Mount Pleasant Academy
Tivoli Gardens
0
1
 
Final
Harbour View
Mount Pleasant Academy
1
1
 
Final
Treasure Beach
Mount Pleasant Academy
2
2
 
Final
Mount Pleasant Academy
Chapelton
5
2
 
Final
Mount Pleasant Academy
Waterhouse
2
1
 
Final
Dunbeholden
Mount Pleasant Academy
0
5
 
Final
Mount Pleasant Academy
Montego Bay United
2
1