| Year | No. of
Finalists | Artist | Title | Subject | Notes |
| 1921 | 45 | | Desbrowe Annear | | |
| 1922 | 53 | | Professor Harrison Moore | | |
| 1923 | 50 | | Portrait of a Lady | | |
| 1924 | 40 | | Miss Collins | | |
| 1925 | 74 | | Maurice Moscovitch | | |
| 1926 | 58 | | Silk and Lace | | |
| 1927 | 56 | | Mrs Annie Murdoch | | |
| 1928 | 66 | | Dr Alexander Leeper | | |
| 1929 | 75 | | The Hon W A Holman, KC | | |
| 1930 | 67 | | Drum-Major Harry McClelland | | |
| 1931 | 74 | | Sir John Sulman | | |
| 1932 | 70 | | Sir William Irvine | | |
| 1933 | | | Ambrose Pratt | | |
| 1934 | 92 | | Self Portrait | | |
| 1935 | 120 | | AB Paterson | | |
| 1936 | 137 | | Dr Julian Smith | | |
| 1937 | 141 | | Self portrait | | |
| 1938 | 145 | | Mme Elink Schuurman | | |
| 1939 | 135 | | Hon G J Bell, C.M.G., D.S.O., V.D., | | |
| 1940 | 156 | | Dr J Forbes McKenzie | | |
| 1941 | 133 | | Sir James Elder, KBE | | |
| 1942 | 111 | | Corporal Jim Gordon, VC | | |
| 1943 | 148 | | Mr Joshua Smith | | |
| 1944 | 185 | | Speaker, House of Representatives, Hon. J. S. Rosevear, M.P. | | |
| 1945 | 197 | | Lt-General The Hon Edmund Herring, KBC, DSO, MC, ED | | |
| 1946 | 80 | | L C Robson, MC, MA | Robson | |
| 1947 | 84 | | Sir Marcus Clark, Kt., K.B.E. | | |
| 1948 | 81 | | Margaret Olley | | |
| 1949 | 81 | | Bonar Dunlop | | |
| 1950 | 86 | | Sir Leslie McConnan | | |
| 1951 | 92 | | Laurie Thomas | Thomas | |
| 1952 | 83 | | Mr Essington Lewis, CH | | |
| 1953 | 72 | | Sir Henry Simpson Newland, CBE, DSO, MS, FRCS | | |
| 1954 | 77 | | Rt. Hon. R. G. Menzies, P.C., C.H., Q.C., M.P. | | |
| 1955 | 88 | | Robert Campbell Esq | | |
| 1956 | 61 | | Mr Albert Namatjira | | |
| 1957 | 69 | | Self portrait | | |
| 1958 | 66 | | Mr Ray Walker | Walker | |
| 1959 | 66 | | Dr Edward MacMahon | MacMahon | |
| 1960 | 80 | | Stanislaus Rapotec | | |
| 1961 | 61 | | Rabbi Dr I. Porush | Israel Porush | |
| 1962 | 81 | | Patrick White | | |
| 1963 | 65 | | Professor James McAuley | | |
| 1964 | | No Award | | | |
| 1965 | 63 | | RA Henderson, Esq | Rupert "Rags" Henderson | |
| 1966 | 71 | | Charles Blackman | | |
| 1967 | 41 | | Margo Lewers | | |
| 1968 | 141 | | Lloyd Rees | | |
| 1969 | 71 | | George Johnston | | |
| 1970 | 15 | | Gruzman – architect | | |
| 1971 | 17 | | Sir John McEwen | | |
| 1972 | 53 | | The Hon E.G. Whitlam | | |
| 1973 | 53 | | Michael Boddy | | |
| 1974 | 50 | | Jockey Norman Stephens | | |
| 1975 | 40 | | The Hon Sir Frank Kitto, KBE | | |
| 1976 | 29 | | Self portrait in the studio | | |
| 1977 | 35 | | Robert Klippel | | |
| 1978 | 39 | | Art, Life and the other thing | | |
| 1979 | 35 | | Portrait of Phillip Adams | | |
| 1980 | | No Award | | | |
| 1981 | 24 | | Rudy Komon | | |
| 1982 | 26 | | Peter Sculthorpe | | |
| 1983 | 28 | | Chandler Coventry | | |
| 1984 | 27 | | Max Gillies | | |
| 1985 | 25 | | Flugelman with Wingman | | |
| 1986 | 26 | | Dr John Arthur McKelvey Shera | Shera | |
| 1987 | 26 | | Equestrian Self Portrait | | |
| 1988 | 25 | | John Beard | | |
| 1989 | 24 | | Portrait of Elwyn Lynn | | |
| 1990 | 31 | | Dorothy Hewett | | |
| 1991/92 | | | The Prime Minister | | |
| 1993 | 27 | | Tom Thompson | | |
| 1994 | 32 | | Homage to John Reichard | Reichard | |
| 1995 | 28 | | Self Portrait with Stunned Mullet | | |
| 1996 | 32 | | Self Portrait – as Diana of Erskineville | | |
| 1997 | 31 | | Barbara Blackman | | |
| 1998 | 29 | | Portrait of Allan Mitelman No 3 | | |
| 1999 | 33 | | Self-portrait/head like a hole | | |
| 2000 | 48 | | Portrait of David Wenham | | |
| 2001 | 31 | | John Bell as King Lear | | |
| 2002 | 31 | | Simon Tedeschi unplugged | | |
| 2003 | 32 | | Richard Flanagan | | |
| 2004 | 40 | | David Gulpilil, two worlds | | |
| 2005 | 36 | | Self portrait Janus Faced | | |
| 2006 | 36 | | The Paul Juraszek Monolith | | |
| 2007 | 41 | | Janet Laurence | | |
| 2008 | 40 | | You are what is most beautiful about me, a self portrait with Kell and Arella | | |
| 2009 | 39 | | Geoffrey Gurrumul Yunupingu | | |
| 2010 | 34 | | Tim Minchin | | |
| 2011 | 41 | | Margaret Olley | | |
| 2012 | 41 | | The Histrionic Wayfarer (after Bosch) | | |
| 2013 | 39 | | hugo | | |
| 2014 | 54 | | Penelope Seidler | | |
| 2015 | 47 | | Judo house pt 6 | | |
| 2016 | 51 | | Barry | | |
| 2017 | 43 | | Agatha Gothe-Snape | | |
| 2018 | 57 | | Self-portrait, after George Lambert | | |
| 2019 | 51 | | Lindy Lee | | |
| 2020 | 51 | | Stand Strong for Who You Are | | |
| 2021 | 52 | Peter Wegner | Portrait of Guy Warren at 100 | Guy Warren | |
| 2022 | 52 | Blak Douglas | Moby Dickens | Karla Dickens | |
| 2023 | 57 | Julia Gutman | Head in the sky, feet on the ground | Montaigne | |
| 2024 | 57 | Laura Jones | Tim Winton | Tim Winton | |
| 2025 | 57 | Julie Fragar | Flagship Mother Multiverse | Justene Williams | |