| Year | Premier |
| 2020 | Mosman |
| 2019 | Mosman |
| 2018 | Mosman |
| 2017 | Mosman |
| 2016 | Not Contested |
| 2015 | Colleagues |
| 2014 | Colleagues |
| 2013 | Old Ignatians |
| 2012 | Knox |
| 2011 | Colleagues |
| 2010 | Drummoyne |
| 2009 | Campbelltown |
| 2008 | Old Ignatians |
| 2007 | St Patrick's |
| 2006 | Old Ignatians |
| 2005 | Old Ignatians |
| 2004 | Old Ignatians |
| 2003 | Old Ignatians |
| 2002 | Colleagues |
| 2001 | Old Ignatians |
| 2000 | Forest |
| 1999 | Old Ignatians |
| 1998 | St Patrick's |
| 1997 | Waverley |
| 1996 | Colleagues |
| 1995 | Mosman |
| 1994 | Colleagues |
| 1993 | Matraville |
| 1992 | Matraville |
| 1991 | Matraville |
| 1990 | Newport |
| 1989 | Waverley |
| 1988 | Waverley |
| 1987 | Waverley |
| 1986 | Waverley |
| 1985 | Newport |
| 1984 | Colleagues |
| 1983 | Waverley |
