Year Winner Country
2018 Portmore United Portmore United Jamaica Jamaica
2017 Arnett Gardens Arnett Gardens Jamaica Jamaica
2016 Montego Bay United FC Montego Bay United FC Jamaica Jamaica
2015 Arnett Gardens Arnett Gardens Jamaica Jamaica
2014 Montego Bay United FC Montego Bay United FC Jamaica Jamaica
2013 Harbour View Harbour View Jamaica Jamaica
2012 Portmore United Portmore United Jamaica Jamaica
2011 Tivoli Gardens Tivoli Gardens Jamaica Jamaica
2010 Harbour View Harbour View Jamaica Jamaica
2009 Tivoli Gardens Tivoli Gardens Jamaica Jamaica
2008 Portmore United Portmore United Jamaica Jamaica
2007 Harbour View Harbour View Jamaica Jamaica
2006 Waterhouse FC Waterhouse FC Jamaica Jamaica
2005 Portmore United Portmore United Jamaica Jamaica
2004 Tivoli Gardens Tivoli Gardens Jamaica Jamaica
2003 Hazard United Hazard United Jamaica Jamaica
2002 Arnett Gardens Arnett Gardens Jamaica Jamaica
2001 Arnett Gardens Arnett Gardens Jamaica Jamaica
2000 Harbour View Harbour View Jamaica Jamaica
1999 Tivoli Gardens Tivoli Gardens Jamaica Jamaica
1998 Waterhouse FC Waterhouse FC Jamaica Jamaica
1997 Seba United Seba United Jamaica Jamaica
1996 Violet Kickers Violet Kickers Jamaica Jamaica
1995 Reno FC Reno FC Jamaica Jamaica
1994 Violet Kickers Violet Kickers Jamaica Jamaica
1993 Hazard United Hazard United Jamaica Jamaica
1992 Wadadah FC Wadadah FC Jamaica Jamaica
1991 Reno FC Reno FC Jamaica Jamaica
1990 Reno FC Reno FC Jamaica Jamaica
1989 Boys' Town Boys' Town Jamaica Jamaica
1988 Wadadah FC Wadadah FC Jamaica Jamaica
1987 Seba United Seba United Jamaica Jamaica
1986 Boys' Town Boys' Town Jamaica Jamaica
1985 Defence Force Defence Force Jamaica Jamaica
1984 Boys' Town Boys' Town Jamaica Jamaica
1983 Tivoli Gardens Tivoli Gardens Jamaica Jamaica
1981 Cavalier FC Cavalier FC Jamaica Jamaica
1980 Santos Santos Jamaica Jamaica
1978 Arnett Gardens Arnett Gardens Jamaica Jamaica
1977 Santos Santos Jamaica Jamaica
1976 Santos Santos Jamaica Jamaica
1975 Santos Santos Jamaica Jamaica
1974 Santos Santos Jamaica Jamaica