Premiers - Judd Cup
| Year | Premier |
| 2022 | Blue Mountains |
| 2021 | Not Contested |
| 2020 | Mosman |
| 2019 | Waverley |
| 2018 | Colleagues |
| 2017 | Knox |
| 2016 | Colleagues |
| 2015 | St Patrick's |
| 2014 | St Patrick's |
| 2013 | St Patrick's |
| 2012 | Colleagues |
| 2011 | Colleagues |
| 2010 | Colleagues |
| 2009 | Old Ignatians |
| 2008 | Old Ignatians |
| 2007 | Mosman |
| 2006 | Old Ignatians |
| 2005 | Old Ignatians |
| 2004 | Old Ignatians |
| 2003 | Old Ignatians |
| 2002 | Old Ignatians |
| 2001 | St Patrick's |
| 2000 | St Patrick's |
| 1999 | St Patrick's |
| 1998 | Waverley |
| 1997 | Old Ignatians |
| 1996 | Colleagues |
| 1995 | Waverley |
| 1994 | Waverley |
| 1993 | Penrith |
| 1992 | Waverley |
| 1991 | Waverley |
| 1990 | Waverley |
| 1989 | Waverley |
| 1988 | Waverley |
| 1987 | Matraville |
| 1986 | Blue Mountains |
| 1985 | Hunters Hill |
| 1984 | Colleagues |
| 1983 | Hunters Hill |
| 1982 | Waverley |
| 1981 | Waverley |
| 1980 | Hunters Hill |
| 1979 | Hunters Hill |
| 1978 | King's Old Boys |
| 1977 | Lane Cove |
| 1976 | St Patrick's |
| 1975 | Bondi |
| 1974 | Bondi |
| 1973 | Petersham |
| 1972 | Lindfield |
| 1971 | Normanhurst Old Boys |
| 1970 | CBOB's |
| 1969 | Newington Old Boys |
| 1968 | Lane Cove |
| 1967 | Macquarie University |
| 1966 | Colleagues |
| 1965 | Dundas |
| 1964 | Pennant Hills |
| 1963 | Lindfield |
| 1962 | University of NSW |
| 1961 | Petersham |
