| 2010/11 | 2011/12 | 2012/13 | 2013/14 | 2014/15 | 2015/16 | 2016/17 | 2017/18 | 2018/19 | 2019/20 |
| 2000/01 | 2001/02 | 2002/03 | 2003/04 | 2004/05 | 2005/06 | 2006/07 | 2007/08 | 2008/09 | 2009/10 |
| 1990/91 | 1991/92 | 1992/93 | 1993/94 | 1994/95 | 1995/96 | 1996/97 | 1997/98 | 1998/99 | 1999/00 |
| 1980/81 | 1981/82 | 1982/83 | 1983/84 | 1984/85 | 1985/86 | 1986/87 | 1987/88 | 1988/89 | 1989/90 |
| 1973/74 | 1974/75 | 1975/76 | 1976/77 | 1977/78 | 1978/79 | 1979/80 |
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JAM Men's League Champions: 1973/74 Santos FC 1974/75 Santos FC 1975/76 Santos FC 1976/77 Santos FC 1977/78 Arnett Gardens FC 1978/79 not held 1979/80 Santos FC 1980/81 Cavalier FC 1981/82 not held 1982/83 Tivoli Gardens FC 1983/84 Boys' Town FC 1984/85 Jamaica Defence Force 1985/86 Boys' Town FC 1986/87 Seba United FC 1987/88 Wadadah FC 1988/89 Boys' Town FC 1989/90 Reno FC 1990/91 Reno FC 1991/92 Wadadah FC 1992/93 Hazard United FC 1993/94 Violet Kickers FC 1994/95 Reno FC 1995/96 Violet Kickers FC 1996/97 Seba United FC 1997/98 Waterhouse FC 1998/99 Tivoli Gardens FC 1999/00 Harbour View FC 2000/01 Arnett Gardens FC 2001/02 Arnett Gardens FC 2002/03 Hazard United FC 2003/04 Tivoli Gardens FC 2004/05 Portmore United FC 2005/06 Waterhouse FC 2006/07 Harbour View FC 2007/08 Portmore United FC 2008/09 Tivoli Gardens FC 2009/10 Harbour View FC 2010/11 Tivoli Gardens FC 2011/12 Portmore United FC 2012/13 Harbour View FC 2013/14 Montego Bay United FC 2014/15 Arnett Gardens FC 2015/16 Montego Bay United FC 2016/17 |
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