| Year | Champion |
| 2000 | W Connection |
| 2001 | W Connection |
| 2002 | San Juan Jabloteh |
| 2003-04 | San Juan Jabloteh |
| 2004 | North East Stars |
| 2005 | W Connection |
| 2006 | Joe Public |
| 2007 | San Juan Jabloteh |
| 2008 | San Juan Jabloteh |
| 2009 | Joe Public |
| 2010-11 | Defence Force |
| 2011-12 | W Connection |
| 2012-13 | Defence Force |
| 2013-14 | W Connection |