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National Premier League .:. List of winners
| Year | Winner | |
| 2013 |
|
Harbour View |
| 2012 |
|
Portmore United |
| 2011 |
|
Tivoli Gardens |
| 2010 |
|
Harbour View |
| 2009 |
|
Tivoli Gardens |
| 2008 |
|
Portmore United |
| 2007 |
|
Harbour View |
| 2006 |
|
Waterhouse FC |
| 2005 |
|
Portmore United |
| 2004 |
|
Tivoli Gardens |
| 2003 |
|
Hazard United |
| 2002 |
|
Arnett Gardens |
| 2001 |
|
Arnett Gardens |
| 2000 |
|
Harbour View |
| 1999 |
|
Tivoli Gardens |
| 1998 |
|
Waterhouse FC |
| 1997 |
|
Seba United |
| 1996 |
|
Violet Kickers |
| 1995 |
|
Reno United |
| 1994 |
|
Violet Kickers |
| 1993 |
|
Hazard United |
| 1992 |
|
Wadadah FC |
| 1991 |
|
Reno United |
| 1990 |
|
Reno United |
| 1989 |
|
Boys' Town |
| 1988 |
|
Wadadah FC |
| 1987 |
|
Seba United |
| 1986 |
|
Boys' Town |
| 1985 |
|
Defence Force |
| 1984 |
|
Boys' Town |
| 1983 |
|
Tivoli Gardens |
| 1981 |
|
Cavalier FC |
| 1980 |
|
Santos |
| 1978 |
|
Arnett Gardens |
| 1977 |
|
Santos |
| 1976 |
|
Santos |
| 1975 |
|
Santos |
| 1974 |
|
Santos |
