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The Charles Sutton Medal is awarded to the player adjudged Best and Fairest for the Western Bulldogs. Scott West holds the record at the club, winning seven medals, followed by Gary Dempsey, with six. It is named after 1950 winner Charlie Sutton, who was the Bulldogs' 1954 premiership captain.

Past winners :

• 2009 - Matthew Boyd
• 2008 - Daniel Cross
• 2007 - Brian Harris
• 2006 - Brad Johnson
• 2005 - Scott West
• 2004 - Scott West
• 2003 - Scott West
• 2002 - Brad Johnson
• 2001 - Luke Darcy
• 2000 - Scott West
• 1999 - Brad Johnson
• 1998 - Scott West
• 1997 - Scott West
• 1996 - Chris Grant, Jose Romero
• 1995 - Scott West
• 1994 - Chris Grant
• 1993 - Leon Cameron
• 1992 - Scott Wynd
• 1991 - Tony Liberatore
• 1990 - Peter Foster
• 1989 - Terry Wallace
• 1988 - Terry Wallace
• 1987 - Tony McGuinness
• 1986 - Brad Hardie
• 1985 - Doug Hawkins
• 1984 - Andrew Purser
• 1983 - Brian Royal
• 1982 - Ian Dunstan
• 1981 - Ian Dunstan
• 1980 - Kelvin Templeton
• 1979 - Ian Dunstan
• 1978 - Kelvin Templeton
• 1977 - Gary Dempsey
• 1976 - Gary Dempsey
• 1975 - Gary Dempsey
• 1974 - Gary Dempsey
• 1973 - Gary Dempsey
• 1972 - Peter Welsh
• 1971 - David Thorpe
• 1970 - Gary Dempsey
• 1969 - George Bisset
• 1968 - David Thorpe
• 1967 - John Jillard
• 1966 - John Schultz
• 1965 - John Schultz
• 1964 - John Schultz
• 1963 - Ray Walker
• 1962 - John Schultz
• 1961 - Ted Whitten
• 1960 - John Schultz
• 1959 - Ted Whitten
• 1958 - Ted Whitten
• 1957 - Ted Whitten
• 1956 - Don Ross
• 1955 - Peter Box
• 1954 - Ted Whitten
• 1953 - Harvey Stevens
• 1952 - Jack Collins
• 1951 - Jack Collins
• 1950 - Charlie Sutton
• 1949 - Wally Donald
• 1948 - Harry Hickey
• 1947 - Joe Ryan
• 1946 - Joe Ryan
• 1945 - Harry Hickey at the time the award was known as the Con Curtain trophy.
• 1944 - Arthur Olliver
• 1943 - Allan Collins
• 1942 - Ted Ellis at the time the award was known as the Con Curtain trophy.
• 1941 - Norm Ware, Arthur Olliver
• 1940 - Norm Ware
• 1939 - Harry Hickey at the time the award was known as the McCarthy trophy.
• 1938 - Norm Ware
• 1937 - Norm Ware
• 1936 - Alby Morrison
• 1935 - George Bennett
• 1934 - Norm Ware
• 1933 - Alby Morrison
• 1932 - Ivan McAlpine
• 1931 - Allan Hopkins
• 1930 - Ivan McAlpine
• 1929 - Bill Russ
• 1928 - Alby Outen
• 1927 - Ivan McAlpine