| Year | Premier | |
| 2019 | Not Contested | |
| 2018 | Merrylands | Div 5 2nd Grade |
| 2017 | Lane Cove | Div 5 2nd Grade |
| 2016 | Not Contested | |
| 2015 | Menai | Div 6 South |
| 2014 | Not Contested | |
| 2013 | Roseville | Div 5 2nd Grade |
| 2012 | Fairvale | Div 5 2nd Grade |
| 2011 | Fairvale | Div 5 2nd Grade |
| 2010 | Rouse Hill | Div 5 2nd Grade |
| 2009 | Liverpool | Div 5 2nd Grade |
| 2008 | Oakhill | Div 5 2nd Grade |
| 2007 | Bankstown | Div 5 2nd Grade |
| 2006 | Colleagues | Div 5 2nd Grade |
| 2005 | Roseville | Div 5 2nd Grade |
| 2004 | Matraville | Div 5 2nd Grade |
| 2003 | Bankstown | Div 5 2nd Grade |
| 2002 | Lidcombe | Div 5 2nd Grade |
| 2001 | Burraneer | Div 5 2nd Grade |
| 2000 | Liverpool | Div 5 2nd Grade |
| 1999 | Burraneer | Div 5 2nd Grade |
| 1998 | Marrickville | Div 5 2nd Grade |
| 1997 | Liverpool | Div 5 2nd Grade |
| 1996 | Sydney Pioneer | Div 5 2nd Grade |
| 1995 | Marrickville | Div 5 1st Grade |
| 1994 | Marrickville | Div 4 2nd Grade |
| 1993 | Merrylands | Div 4 2nd Grade |
| 1992 | Middle Harbour Skiff Club | Div 4 2nd Grade |
| 1991 | Newington Old Boys | Div 4 2nd Grade |
| 1990 | Tempe | Div 4 2nd Grade |
| 1989 | Sydney High Old Boys | Div 4 2nd Grade |
| 1988 | Newington Old Boys | Div 4 2nd Grade |
| 1987 | Smithfield | Div 4 2nd Grade |
| 1986 | Cammeray-Northbridge & Northmead (joint) | Div 4 2nd Grade |
| 1985 | Cavaliers | Div 4 2nd Grade |
| 1984 | North Sydney High Old Boys | Div 4 2nd Grade |
| 1983 | Haberfield | Div 4 2nd Grade |
| 1982 | North Sydney Old Boys | Div 4 2nd Grade |
| 1981 | Northmead | Div 4 2nd Grade |
| 1980 | Tobians | Div 4 2nd Grade |
| 1979 | CBC Bank | Div 4 2nd Grade |
| 1978 | Willoughby | Div 4 2nd Grade |
| 1977 | Merrylands | Div 4 2nd Grade |
| 1976 | Blacktown Old Boys | Div 4 2nd Grade |
| 1975 | Matraville Old Boys | |
| 1974 | Manly Life Savers | |
| 1973 | Punchbowl |
