The Bob Skilton Medal is awarded to the Sydney Swans player adjudged the Best and Fairest over the home and away season. It is named after Bob Skilton, who won the award a record 9 times. The Sydney Swans are an Australian Football League (AFL) club based in Sydney, New South Wales. ... Best and Fairest is the phrase given to players in the Australian Football League (formerly the VFL) that are adjudged to have played the best during the season without being suspended. ... Bob Skilton (born 1938) was an Australian Rules football player who played as a rover for South Melbourne and Victoria between 1956 and 1971. ...