1921

William B Mcinnes

Desbrowe Annear

1922

William B Mcinnes

Professor Harrison Moore

1923

William B Mcinnes

Portrait of a lady

1924

William B Mcinnes

Portrait of Miss Collins

1925

John Longstaff

Portrait of Maurice Moscovitch

1926

William B Mcinnes

Silk and lace

1927

George W Lambert

Mrs Murdoch

1928

John Longstaff

Portrait of Dr Alexander Leeper

1929

John Longstaff

W A Holman, KC

1930

William B Mcinnes

Drum-Major Harry McClelland

1931

John Longstaff

Sir John Sulman

1932

Ernest Buckmaster

Sir William Irvine

1933

Charles Wheeler

Ambrose Pratt

1934

Henry Hanke

Self portrait

1935

John Longstaff

A B ('Banjo') Paterson

1936

William B Mcinnes

Dr Julian Smith

1937

Normand Baker

Self portrait

1938

Nora Heysen

Mme Elink Schuurman

1939

Max Meldrum

The Hon G J Bell, Speaker, House of Representatives

1940

Max Meldrum

Dr J Forbes McKenzie

1941

William Dargie

Sir James Elder, KBE

1942

William Dargie

Corporal Jim Gordon, VC

1943

Willian Dobell

Joshua Smith

1944

Joshua Smith

S Rosevear, MHR, Speaker

1945

William Dargie

Lt-General The Hon Edmund Herring, KBC, DSO, MC, ED

1946

William Dargie

L C Robson, MC, MA

1947

William Dargie

Sir Marcus Clarke, KBE

1948

William Dobell

Margaret Olley

1949

Arthur Murch

Bonar Dunlop

1950

William Dargie

Sir Leslie McConnan

1951

Ivor Hele

Laurie Thomas

1952

William Dargie

Mr Essington Lewis, CH

1953

Ivor Hele

Sir Henry Simpson Newland, CBE, DSO, MS, FRCS

1954

Ivor Hele

Rt Hon R G Menzies, PC, CH, QC, MP

1955

Ivor Hele

Robert Campbell Esq

1956

William Dargie

Mr Albert Namatjira

1957

Ivor Hele

Self portrait

1958

William Pidgeon

Mr Ray Walker

1959

William Dobell

Dr Edward MacMahon

1960

Judy Cassab

Stanislaus Rapotec

1961

William Pidgeon

Rabbi Dr I Porush

1962

Louis Kahan

Patrick White

1963

Jack Carington Smith

Professor James McAuley

1964

No award

1965

Clifton Pugh

R A Henderson

1966

Jon Molvig

Charles Blackman

1967

Judy Cassab

Margo Lewers

1968

William Pidgeon

Lloyd Rees

1969

Ray Crooke

George Johnston

1970

Eric Smith

Gruzman - architect

1971

Clifton Pugh

Sir John McEwan

1972

Clifton Pugh

The Hon E G Whitlam

1973

Janet Dawson

Michael Boddy

1974

Sam Fullbrook

Jockey Norman Stephens

1975

Kevin Connor

The Hon Sir Frank Kitto, KBE

1976

Brett Whiteley

Self portrait in the studio

1977

Kevin Connor

Robert Klippel

1978

Brett Whiteley

Art, life and the other thing

1979

Wes Walters

Portrait of Phillip Adams

1980

No award

1981

Eric Smith

Rudy Komon

1982

Eric Smith

Peter Sculthorpe

1983

Nigel Thomson

Chandler Coventry

1984

Keith Looby

Max Gillies

1985

Guy Warren

Flugelman with Wingman

1986

Davida Allen

Dr John Arthur McKelvey Shera

1987

William Robinson

Equestrian self portrait

1988

Fred Cress

John Beard

1989

Bryan Westwood

Portrait of Elwyn Lynn

1990

Geoffrey Proud

Dorothy Hewett

1991/92

Bryan Westwood

The Prime Minister

1992/93

Garry Shead

Tom Thompson

1993/94

Francis Giacco

Homage to John Reichard

1995

William Robinson

Self portrait with stunned mullet

1996

Wendy Sharpe

Self portrait - as Diana of Erskineville

1997

Nigel Thomson

Barbara Blackman

1998

Lewis Miller

Portrait of Allan Mitelman No 3

1999

Euan MacLeod

Self portrait/head like a hole

(Highly commended: Adam Cullen Max Cullen)

2000

Adam Cullen

Portrait of David Wenham

(Highly commended: Jenny Sages Each morning when I wake up I put on my Mother's face and Garry Shead Sasha Grishin)

2001

Nicholas Harding

John Bell as King Lear

(Highly commended: Jenny Sages Jackie and Kerryn)

2002

Cherry Hood

Simon Tedeschi unplugged

2003

Geoffrey Dyer

Richard Flanagan

2004

Craig Ruddy

David Gulpilil, two worlds

2005

John Olsen

Self portrait Janus faced

2006

Marcus Wills

The Paul Juraszek monolith (after Marcus Gheeraerts)

2007

John Beard

Janet Laurence

2008

Del Kathryn Barton

You are what is most beautiful about me, a self portrait with Kell and Arella

(Highly commended: Vincent Fantauzzo Heath)