| Year | Champion |
| 1998-99 | Tivoli Gardens FC |
| 1999-00 | Harbour View FC |
| 2001-02 | Arnett Gardens |
| 2002-03 | Hazard United |
| 2004-05 | Harbour View FC |
| 2005-06 | Waterhouse FC |
| 2006-07 | Harbour View FC |
| 2007-08 | Portmore United |
| 2008-09 | Tivoli Gardens FC |
| 2009-10 | Harbour View FC |
| 2010-11 | Tivoli Gardens FC |
| 2011-12 | Portmore United |
| 2012-13 | Harbour View FC |
| 2013-14 | Montego Bay United |