| Year |
Winning Artist 1 |
Work 1 |
Winning Artist 2 |
Work 2 |
Notes |
| 1920 | Kate Campbell Muirhead | Elizabeth | David Macbeth Sutherland | The Painting Student | Muirhead's work was a bust sculpture, Sutherland's work a painting.[4][5][6]
[7] |
| 1921 | Cecile Walton | To Nobody Knows Where | | | [8] |
| 1922 | John Rankine Barclay | The Artist's Wife | | | [9] |
| 1923 | James Wallace Ferguson | A Visitor | | | [10] |
| 1924 | Donald Moodie | Autumn Day | George William Salvesen | The Dance | Moodie for a painting, Salvesen for a sculpture.[11][12] |
| 1925 | Laelia Armine Cockburn | A Rough Lot for Sale | | | [13] |
| 1926 | David Shanks Ewart | The Toilers | | | [14] |
| 1927 | Ancell Stronach | The Unexpected Meeting | | | [15] |
| 1928 | William Crozier | The 'Cello Player | Margaret Findlay | The Bathers | Findlay's work a sculpture, Crozier's work a painting.[16][17][18] |
| 1929 | William Lamb | Ferryden Fisher Wife | | | A sculpture.[19] |
| 1930 | Robert Sivell | Miss Jean O. H. Morton | | | [20] |
| 1931 | Ian Campbell | Self Portrait | | | [21] |
| 1932 | Alister Maitland | Alice Ann | | | He was noted at the time as the youngest winner, aged 21.[22] |
| 1933 | Thomas Whalen | The Amazon | | | For 3 sculpture works The Amazon, Mother's Kisses, and Torso.[23] |
| 1934 | William Wilson | The Alcazar, Segovia | | | For a group of Wilson's work. The named piece was a drawing. Wilson was a noted engraver.[24] |
| 1935 | James McIntosh Patrick | Marion | | | [25] |
| 1936 | Alexander George Oliphant | David Kerr Esq. | | | [26] |
| 1937 | Mary Nicol Neill Armour | Cantaloupe | | | [27] |
| 1938 | Ian Fleming | The Painters: McBryde and Colquhoun | | | [28] |
| 1939 | William Drummond Bone | Leisure | | | [29] |
| 1940 | Scott Sutherland | Labor Vincit | | | A sculpture.[30] |
| 1941 | David Abercrombie Donaldson | Alfred | | | [31] |
| 1942 | James Alan Davie | Brenda Mark | | | [32] |
| 1943 | Alberto Morrocco | Leon | Colin Gibson | Lisbeth | [33] |
| 1944 | Margaret Kennedy Mackenzie | Pieta | Gordon Stewart Cameron | Boy with Apple | Mackenzie's work was sculpture, Cameron's work was a painting.[34] |
| 1945 | Robert Henderson Blyth | Winter in Walkerburn, 1939 | | | [35] |
| 1946 | George William Lennox Paterson | Frank Tweedie and the Birds | | | [36] |
| 1947 | James Hillocks | Portrait of my Mother | | | [37] |
| 1948 | Sinclair Thomson | The White Shawl | | | [38] |
| 1949 | Alistair J. T. Paterson | Still Life | | | [39] |
| 1950 | Tom M. Macnair | Jean Hannan | | | A terracotta sculpture of a head.[40] |
| 1951 | Robin Philipson | Brenda, Spring Portrait | | | [41] |
| 1952 | Ellen Malcolm | Portrait of a Young Man | | | [42] |
| 1953 | William Alexander Burns | Sunday | | | [43] |
| 1954 | Ann Henderson | Composition | | | A sculpture.[44] |
| 1955 | Brenda Clouston | Youth | | | A sandstone sculpture.[45] |
| 1956 | David McClure | ? | | | McClure exhibited five works:- Harbour, Millport; The Green Hill; Trees, Millport; Self portrait; and Flowers At A Window.[46] |
| 1957 | Brenda Mark | Figures In Moonlight | | | [47] |
| 1958 | Margot Sandeman | The Walk Across The Fields | | | [48] |
| 1959 | Jean Fleming | ?Landscape painting | | | [49] |
| 1960 | John Houston | Pigeons and Village | David Alan Redpath Michie | Red Flower | [50] |
| 1961 | William Hunter Littlejohn | Painting 1960 | | | Littlejohn had 3 paintings at the exhibition; the other two being White Glass and Green Bottle, each a still life work. Littlejohn considered that it was his abstract work Painting 1960 that had won the Guthrie Award.[51] |
| 1962 | Elizabeth Blackadder | Still Life on a White Table | | | Blackadder had another two works: Auray; and Breton Church.[52][53] |
| 1963 | Alex Campbell | Rehearsal | | | [54] |
| 1964 | Bill Scott | Seated Figure | | | A sculpture.[55] |
| 1965 | Robert Callender | Ludo | | | [56] |
| 1966 | George Alexander Macpherson | ? | | | [57] |
| 1967 | Archibald Dunbar McIntosh | ? | | | [58] |
| 1968 | John Knox | Swing and Stool - After Uccello | | | [59] |
| 1969 | Alexander Fraser | Shankar at the Blue Piggery | | | [60] |
| 1970 | Leon Morrocco | Figure in a Bedroom | | | [61][62] |
| 1971 | Ian McKenzie Smith | Reflections (Harbour) | | | [63] |
| 1972 | Frances Pelly | Greenheart Woman | | | [64] |
| 1973 | George Donald | Virginia's Quilt | | | A padded canvas work.[65] |
| 1974 | ? | ? | | | |
| 1975 | ? | ? | | | |
| 1976 | | | | Award withheld.[66] |
| 1977 | Barbara Rae | Sea Dreamers | | | [67][66] |
| 1978 | Ian Howard | Misdirection | | | [68] |
| 1979 | Ronald Forbes | ? | | | Forbes exhibited two works: All Set; and Scarecrow[69] |
| 1980 | ? | ? | | | |
| 1981 | Martin Churchill | Palace Hotel | | | [70][71] |
| 1982 | John Mooney | ? | | | [72] |
| 1983 | Ian Robertson | ? | | | [73][74][75] |
| 1984 | Lennox Dunbar | Sweep | | | [76] |
| 1985 | David Cook | Fooled You | | | [77][78] |
| 1986 | ? | ? | | | |
| 1987 | Fiona Dean | Still Life With Work Objects | | | [79][80] |
| 1988 | ? | ? | | | |
| 1989 | Jacqui Miller Nixon | Warrior | | | [81] |
| 1990 | Joseph Davie | ? | | | Davie submitted two works:- A Journal Of The Blackout: Unwelcome Heroes; and The Spirit Of The Community[82] |
| 1991 | ? | ? | | | |
| 1992 | ? | ? | | | |
| 1993 | David Hosie | ? | | | [83] |
| 1994 | Joe Fan | In Evil Hours | | | [84] |
| 1995 | Philip Braham | ? | | | [85] |
| 1996 | Robbie Bushe | Laughing Boys, Tomorrow They Will Be Gone | | | [86] |
| 1997 | Stephen Mangan | ? | | | [87] |
| 1998 | Barry McGlashan | ? | | | [88] |
| 1999 | Alasdair Wallace | Field | | | [89][90] |
| 2000 | Delia Baillie | Fantasies of the Dustbin | | | [91] |
| 2001 | Kevin Dagg | ? | | | A sculpture.[92] |
| 2002 | ? | ? | | | |
| 2003 | ? | ? | | | |
| 2004 | Steven MacIver | ? | | | [93] |
| 2005 | ? | ? | | | |
| 2006 | Heather Ross | ? | | | [94][95] |
| 2007 | Heather Ross | ? | | | [94][95] |
| 2008 | Trine Pedersen | ? | | | [96] |
| 2009 | Sharon Thomas | ? | | | [97] |
| 2010 | ? | ? | | | |
| 2011 | Briony Anderson | ? | | | [98] |
| 2012 | ? | ? | | | |
| 2013 | ? | ? | | | |
| 2014 | Julie-Ann Simpson | Among Silver Birches | | | [99] |
| 2015 | Georgia Rose Murray | Rainbow Trout Cormorant Noir | | | [100] |
| 2016 | Emily Moore | ? | | | [101] |
| 2017 | Kristina Chan | Leith Theatre, The Stage | | | A laser etched woodcut.[102] |
| 2018 | Ed Compson | Shutterstock Infinity Klee | | | An oil & laser etching on board.[103] |
| 2019 | Julie-Ann Simpson | Stings To Be Gathered | | | [104] |
| 2020 | | | | | Online exhibition due to coronavirus pandemic |
| 2021 | Emily Beaney | Breaking the Fall | | | A trilogy of experimental documentaries.[105][106] |
| 2022 | Claire Moore | The Murder of Mr Muster | | | [107] |
| 2023 | Daniel Nelis | Dark Turned Fields | | | [108] |
| 2024 | Rae-Yen Song | Song Dynasty Beast | | | Sculptural costume[109] |
| 2025 | James Howden | Tyrant | | | Sculpture |