| Year | Premier |
| 2019 | Hunters Hill |
| 2018 | St Patrick's |
| 2017 | Hills |
| 2016 | Hills |
| 2015 | Hills |
| 2014 | UNSW |
| 2013 | UNSW |
| 2012 | Newport |
| 2011 | Newport |
| 2010 | Waverley |
| 2009 | Waverley |
| 2008 | Lindfield |
| 2007 | Beecroft |
| 2006 | Beecroft & Hornsby (joint) |
| 2005 | Liverpool |
| 2004 | Liverpool |
| 2003 | Campbelltown |
| 2002 | Beecroft |
| 2001 | Newport |
| 2000 | Waverley |
| 1999 | Hornsby |
| 1998 | Lindfield |
| 1997 | Lindfield |
| 1996 | Old Ignatians |
| 1995 | Old Ignatians |
| 1994 | King's Old Boys |
| 1993 | St Ives |
| 1992 | Briars |
| 1991 | St Ives |
| 1990 | St Leo's |
| 1989 | St Leo's |
| 1988 | Knox Old Boys |
| 1987 | Lindfield |
| 1986 | Waverley & Knox Old Boys (joint) |
| 1985 | Waverley |
| 1984 | Matraville |
| 1983 | Sydney High Old Boys |
| 1982 | Sydney High Old Boys |
| 1981 | Sydney High Old Boys |
| 1980 | Guild Teachers Old Boys |
| 1979 | Normanhurst Old Boys |
| 1978 | Bondi-Bronte |
| 1977 | Killara |
| 1976 | Roseville Castle Cove |
| 1975 | Willoughby |
| 1974 | Normanhurst Old Boys |
| 1973 | Trinity Old Boys |
| 1972 | Haberfield |
| 1971 | Beecroft |
