TheBob Skilton Medal is an annual Australian rules football award presented to the player(s) adjudged thebest and fairest at theSydney Swans (formerly the South Melbourne Football Club) throughout theVictorian Football League/Australian Football League (VFL/AFL) season. It is named afterBob Skilton, who won the award a record nine times from 1958 to 1968. The voting system, as of the2017 AFL season, involves five coaches giving an undetermined number of players up to ten votes each after every match. Players can receive a maximum of 50 votes for a game.[1]
| ^ | Denotes current player |
| + | Player wonBrownlow Medal in same season |
| ^ | Denotes current player |
| Player | Medals | Seasons |
|---|---|---|
| Bob Skilton | 9 | 1958, 1959, 1961, 1962, 1963, 1964, 1965, 1967, 1968 |
| Peter Bedford | 5 | 1969, 1970, 1971, 1973, 1975 |
| Herbie Matthews | 5 | 1936, 1937, 1939, 1940, 1943 |
| Paul Kelly | 4 | 1992, 1993, 1996, 1997 |
| Ron Clegg | 3 | 1948, 1949, 1951 |
| Adam Goodes | 3 | 2003, 2006, 2011 |
| Gerard Healy | 3 | 1986, 1987, 1988 |
| Josh Kennedy | 3 | 2012, 2015, 2016 |
| Luke Parker | 3 | 2014, 2017, 2021 |
| Bill Williams | 3 | 1946, 1947, 1950 |
| David Ackerly | 2 | 1980, 1982 |
| Jim Cleary | 2 | 1942, 1944 |
| Isaac Heeney^ | 2 | 2024, 2025 |
| Ron Hillis | 2 | 1930, 1935 |
| Brett Kirk | 2 | 2005, 2007 |
| Jake Lloyd^ | 2 | 2018, 2020 |
| Jarrad McVeigh | 2 | 2008, 2013 |
| Barry Round | 2 | 1979, 1981 |
| Jim Taylor | 2 | 1953, 1957 |
| Len Thomas | 2 | 1931, 1938 |
| Paul Williams | 2 | 2001, 2002 |
| Stephen Wright | 2 | 1985, 1990 |
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