| Year |
Premier |
| 2020 |
Drummoyne |
| 2019 |
Mosman |
| 2018 |
Petersham |
| 2017 |
Petersham |
| 2016 |
Mosman |
| 2015 |
Balmain |
| 2014 |
St Patrick's |
| 2013 |
Balmain & St Patrick's (joint) |
| 2012 |
Drummoyne |
| 2011 |
Colleagues |
| 2010 |
Drummoyne |
| 2009 |
Knox Old Boys |
| 2008 |
Drummoyne |
| 2007 |
Drummoyne |
| 2006 |
Drummoyne |
| 2005 |
Knox Old Boys |
| 2004 |
Drummoyne |
| 2003 |
Dundas Valley |
| 2002 |
Old Ignatians |
| 2001 |
St Ives |
| 2000 |
Drummoyne |
| 1999 |
Newport |
| 1998 |
University of NSW |
| 1997 |
Hunters Hill |
| 1996 |
Colleagues |
| 1995 |
Hunters Hill |
| 1994 |
University of NSW |
| 1993 |
St Patrick's |
| 1992 |
St Leo's |
| 1991 |
Waverley & Matraville (joint) |
| 1990 |
Waverley |
| 1989 |
Waverley |
| 1988 |
Matraville |
| 1987 |
Hunters Hill |
| 1986 |
Matraville |
| 1985 |
Matraville |
| 1984 |
Colleagues |
| 1983 |
Bronte |
| 1982 |
Colleagues |
| 1981 |
Hunters Hill |
| 1980 |
Colleagues |
| 1979 |
Hunters Hill |
| 1978 |
Hunters Hill |
| 1977 |
Hunters Hill |
| 1976 |
St Ives |
| 1975 |
St Patrick's |
| 1974 |
Petersham |
| 1973 |
Petersham |
| 1972 |
Hunters Hill |
| 1971 |
Bondi Life Savers |
| 1970 |
Colleagues |
| 1969 |
Newington Old Boys |
| 1968 |
Lane Cove |
| 1967 |
Lane Cove |
| 1966 |
Colleagues |
| 1965 |
Briars |
| 1964 |
Briars |
| 1963 |
Colleagues |
| 1962 |
Colleagues |
| 1961 |
University of NSW |
| 1960 |
Colleagues |
| 1959 |
Colleagues |
| 1958 |
Western Suburbs |
| 1957 |
Colleagues |
| 1956 |
Western Suburbs |
| 1955 |
Colleagues |
| 1954 |
Mosman |
| 1953 |
Western Suburbs |
| 1952 |
Briars |
| 1951 |
Moore Park |
| 1950 |
Colleagues |
| 1949 |
Briars |
| 1948 |
Concord West |
| 1947 |
Drummoyne |
| 1946 |
Epping |
| 1945 |
Not Contested |
| 1944 |
Not Contested |
| 1943 |
Not Contested |
| 1942 |
Not Contested |
| 1941 |
Colleagues |
| 1940 |
Briars |
| 1939 |
Bondi Life Savers & Royal Aus Artillery (joint) |
| 1938 |
NSW Fire Brigades |
| 1937 |
Bondi Life Savers |
| 1936 |
North Steyne |
| 1935 |
Roseville |
| 1934 |
Petersham |
| 1933 |
Coogee |
| 1932 |
Waverley |
| 1931 |
Coogee |
| 1930 |
NSW Fire Brigades |
| 1929 |
North Steyne |
| 1928 |
Manly Life Savers |
| 1927 |
Mosman |
| 1926 |
Coogee |
| 1925 |
Coogee |
| 1924 |
Manly Life Savers |
| 1923 |
Mosman |
