| Year | Category | Winner |
|---|---|---|
| 2016 | Most Outstanding Contribution to Journalism | Bruce Petty |
| 2016 | Best Artwork | David Rowe |
| 2016 | Best Cartoon | Mark Knight |
| 2015 | Best Artwork | Safdar Ahmed |
| 2015 | Best Cartoon | David Pope |
| 2014 | Best Artwork | Eric Lobbecke |
| 2014 | Best Cartoon | Ron Tandberg |
| 2013 | Best Artwork | Pat Campbell |
| 2013 | Best Cartoon | Cathy Wilcox |
| 2012 | Best Artwork | Steven Grice |
| 2012 | Best Cartoon | Andrew Marlton |
| 2011 | Best Artwork | Simon Bosch |
| 2011 | Best Cartoon | David Rowe |
| 2010 | Best Artwork | Eric Lobbecke |
| 2010 | Best Cartoon | Mark Knight |
| 2009 | Best Online Journalism (multimedia) | Maroondah Leader team |
| 2009 | Best Artwork | David Rowe |
| 2009 | Best Cartoon | Peter Nicholson |
| 2008 | Best Artwork | Simon Bosch |
| 2008 | Best Cartoon | Jon Kudelka |
| 2007 | Best Artwork | Sturt Krygsmann |
| 2007 | Best Cartoon | Cathy Wilcox |
| 2006 | Best Artwork | Karl Hilzinger |
| 2006 | Best Cartoon | Alan Moir |
| 2005 | Most Outstanding Contribution to Journalism | The Australian Cartoonists Association |
| 2005 | Best Artwork | Eric Lobbecke |
| 2005 | Best Cartoon | Andrew Dyson |
| 2004 | Best Editorial Graphics and Design | The Australian Design and Graphic Team |
| 2004 | Best Artwork | Andrew Dyson |
| 2004 | Best Cartoon | Mark Knight |
| 2003 | Best Editorial Graphics and Design | Simon Pipe |
| 2003 | Best Artwork | Sturt Krygsman |
| 2003 | Best Cartoon | Mark Knight |
| 2002 | Best Information Graphics or Digital Photo Illustration | Bill Farr |
| 2002 | Best Artwork | Greg Bakes |
| 2002 | Best Cartoon | Bill Leak |
| 2001 | Best Information Graphics or Digital Photo Illustration | SMH Olympics |
| 2001 | Best Artwork | John Spooner |
| 2001 | Best Cartoon | Matt Golding |
| 2000 | Best Information Graphics or Digital Photo Illustration | Paul Leigh, Will Pearce & Gary Smart |
| 2000 | Best Artwork | Sturt Krygsman |
| 2000 | Best Cartoon | Alan Moir |
| 1999 | Best Information Graphics or Digital Photo Illustration | Will Pearce |
| 1999 | Best Artwork | Donna Maegraith |
| 1999 | Best Cartoon | Jenny Coopes |
| 1998 | Best Information Graphics or Digital Photo Illustration | Will Pearce |
| 1998 | Best Artwork | Tony Edwards |
| 1998 | Best Cartoon | Rod Clement |
| 1997 | Best Information Graphics or Digital Photo Illustration | Viki Sizgoric |
| 1997 | Best Artwork | Bill Leak |
| 1997 | Best Cartoon | Ron Tandberg |
| 1996 | Best Illustration | Suzanne White |
| 1996 | Best Cartoon | Bill Leak |
| 1995 | Best Illustration | John Shakespeare |
| 1995 | Best Cartoon | Bill Leak |
| 1994 | Best Illustration | John Spooner |
| 1994 | Best Cartoon | John Spooner |
| 1993 | Best Illustration | Eric Löbbecke |
| 1993 | Best Cartoon | Bill Leak |
| 1992 | Best Illustration | Peter Nicholson |
| 1992 | Best Cartoon | Peter Nicholson |
| 1991 | Best Illustration | Peter Nicholson |
| 1991 | Best Cartoon | Dean Alston |
| 1990 | Best Illustration | Bill Leak |
| 1990 | Best Cartoon | Earl Budden |
| 1989 | Best Illustration | Bill Leak |
| 1989 | Best Cartoon | Jenny Coopes |
| 1988 | Best Illustration | Paul Best |
| 1988 | Best Cartoon | Matthew Martin |
| 1987 | Best Illustration | Bill Leak |
| 1987 | Best Cartoon | Geoff Pryor |
| 1986 | Best Illustration | Ward O’Neill |
| 1986 | Best Cartoon | Ron Tandberg (also awarded the Gold Walkley) |
| 1985 | Best Illustration | Jenny Coopes |
| 1985 | Best Cartoon | Ron Tandberg |
| 1984 | Best Illustration | Ward O’Neill |
| 1984 | Best Cartoon | Paul Zanetti |
| 1983 | Best Illustration | John Spooner |
| 1983 | Best Cartoon | Ron Tandberg |
| 1982 | Best Illustration | Ward O’Neill |
| 1982 | Best Cartoon | Peter Nicholson |
| 1981 | Best Illustration | Geoff Pryor |
| 1981 | Best Cartoon | Patrick Cook |
| 1980 | Best Illustration | Neil Moore |
| 1980 | Best Cartoon | Ron Tandberg |
| 1979 | Best Illustration | David Bromley |
| 1979 | Best Cartoon | Ron Tandberg (also awarded the Gold Walkley) |
| 1978 | Best Illustration | David Cox |
| 1978 | Best Cartoon | Stewart McCrae |
| 1977 | Best Illustration | Patrick Cook |
| 1977 | Best Cartoon | Ron Tandberg |
| 1976 | Best Illustration | George Haddon |
| 1976 | Best Cartoon | Ron Tandberg |
| 1975 | Best Illustration | George Haddon |
| 1975 | Best Cartoon | Norm Mitchell |
| 1974 | Best Illustration | George Haddon |
| 1974 | Best Cartoon | Larry Pickering |
| 1973 | Best Illustration | Larry Pickering |
| 1973 | Best Cartoon | Alan Langoulant |
| 1972 | Best Illustration | Theo Batten |
| 1972 | Best Cartoon | Larry Pickering |
| 1971 | Best Illustration | Richard Sealey |
| 1971 | Best Cartoon | Larry Pickering |
| 1970 | Best Press Artwork | Lawrence Green |
| 1970 | Best Illustration | George Haddon |
| 1970 | Best Cartoon | Aubrey Collette |
| 1969 | Best Press Artwork | Charles Altmann |
| 1969 | Best Illustration | Arthur Boothroyd |
| 1969 | Best Cartoon | Paul Rigby |
| 1968 | Best Press Artwork | Gary John Turner |
| 1968 | Best Illustration | Charles Thompson |
| 1968 | Best Cartoon | Cedric Baxter |
| 1967 | Best Press Artwork | Bruce Begg |
| 1967 | Best Illustration | John Petersen |
| 1967 | Best Cartoon | Frank Benier |
| 1966 | Best Press Artwork | Arthur Hudson |
| 1966 | Best Illustration | Arthur McNeil |
| 1966 | Best Cartoon | Paul Rigby |
| 1965 | Best Press Artwork | Arthur Hudson |
| 1965 | Best Illustration | Arthur McNeil |
| 1965 | Best Cartoon | Les Tanner |
| 1964 | Best Press Artwork | Bruce Begg |
| 1964 | Best Illustration | Arthur McNeil |
| 1963 | Best Press Artwork | Arthur Hudson |
| 1963 | Best Illustration | Arthur S. Boothroyd |
| 1963 | Best Cartoon | Paul Rigby |
| 1962 | Best Press Artwork | Rudolph Charles Altmann |
| 1962 | Best Illustration | James G. Phillips |
| 1962 | Best Cartoon | Les Tanner |
| 1961 | Best Press Artwork | Bruce Begg |
| 1961 | Best Illustration | Arthur S.Boothroyd |
| 1961 | Best Cartoon | Paul Rigby |
| 1960 | Best Press Artwork | Bruce Begg |
| 1960 | Best Illustration | J.G. Phillips |
| 1960 | Best Cartoon | Paul Rigby |
| 1959 | Best Press Artwork | Rudolph Charles Altmann |
| 1958 | Best Press Artwork | Rudolph Charles Altmann |
| 1958 | Best Cartoon | Virgil Reilly |