| Year |
Premiers |
| 2019 |
Chatswood |
| 2018 |
Eastern Suburbs |
| 2017 |
Colleagues |
| 2016 |
Lane Cove |
| 2015 |
Not Contested |
| 2014 |
Hills |
| 2013 |
Epping |
| 2012 |
Hills |
| 2011 |
Petersham |
| 2010 |
Blacktown |
| 2009 |
Roseville |
| 2008 |
Not Contested |
| 2007 |
Not Contested |
| 2006 |
Not Contested |
| 2005 |
Not Contested |
| 2004 |
Not Contested |
| 2003 |
Not Contested |
| 2002 |
Not Contested |
| 2001 |
Not Contested |
| 2000 |
Not Contested |
| 1999 |
Not Contested |
| 1998 |
Not Contested |
| 1997 |
North Steyne |
| 1996 |
Not Contested |
| 1995 |
Cook Islands |
| 1994 |
Austral |
| 1993 |
Sylvania |
| 1992 |
Ashfield United |
| 1991 |
Marrickville |
| 1990 |
Northmead |
| 1989 |
Tempe |
| 1988 |
Northmead |
| 1987 |
Middle Harbour Skiff Club |
| 1986 |
Era-Sylvania |
| 1985 |
Kingsgrove North |
| 1984 |
Arncliffe Scots |
| 1983 |
Pennant Hills Old Boys |
| 1982 |
Oatley |
| 1981 |
Coogee |
| 1980 |
Coogee |
| 1979 |
Manly |
| 1978 |
Randwick |
| 1977 |
Maccabi |
| 1976 |
Rockdale |
| |
|
| 1976 - 1995 the Radford Cup was contested by one-team senior clubs |
| In 1997, and since 2009, the Radford Cup has been contested by Colts teams |
