| Year | Premiers |
| 2019 | Redfield Old Boys |
| 2018 | Hawkesbury Ag College |
| 2017 | Epping |
| 2016 | Hawkesbury Ag College |
| 2015 | Redfield Old Boys |
| 2014 | Hills |
| 2013 | St George |
| 2012 | Brothers |
| 2011 | Blue Mountains |
| 2010 | Balmain |
| 2009 | Merrylands |
| 2008 | Blacktown |
| 2007 | Waverley |
| 2006 | Briars |
| 2005 | Epping |
| 2004 | CBOB's |
| 2003 | King's Old Boys |
| 2002 | Liverpool |
| 2001 | Epping |
| 2000 | Petersham |
| 1999 | Dundas Valley |
| 1998 | Canterbury |
| 1997 | Drummoyne |
| 1996 | Ku-Ring-Gai |
| 1995 | Briars |
| 1994 | Not Contested |
| 1993 | Not Contested |
| 1992 | Not Contested |
| 1991 | Not Contested |
| 1990 | Cammeray Northbridge |
| 1989 | Haberfield |
| 1988 | Fairvale Old Boys |
| 1987 | Rockdale |
| 1986 | Rockdale |
| 1985 | Sydney Welsh |
| 1984 | Not Contested |
| 1983 | Wenworthville RSL |
| 1982 | Northmead |
| 1981 | Cammeray |
| 1980 | Willoughby |
| 1979 | Manly Savers & Maccabi (joint) |
| 1978 | Killara |
| 1977 | Manly Silver Ferns |
| 1976 | North Sydney High Old Boys |
| 1975 | Bondi Boys Club |
| 1974 | Bondi Boys Club |
| 1973 | Rockdale |
| 1972 | Bondi Boys Club |
