Whiteford started his senior career with Hibernian, but was unable to establish himself in the first team and was given a free transfer.[6] He signed for Airdrie and served the club with distinction, making over 400 total appearances including the 1975 Scottish Cup Final in which he was captain (lost to Celtic)[6][7] as well as winning 1973–74 Scottish Division Two title and 1976 Spring Cup, plus another runner-up medal from the 1971–72 Texaco Cup. In 2016 he was voted into the Diamonds 'Greatest XI' by supporters.[8]
After retiring as a player, Whiteford managed Albion Rovers, Dumbarton (alongside Alex Wright) and then Airdrieonians.[6] He resigned as Airdrie manager in 1987 because he lost enjoyment for the game, and decided to concentrate on his then principal career as a physical education teacher.[6]
Whiteford died in 2002, aged 54.[6] His uncle Jock[9][10] and cousins Davie and Jocky Whiteford (a teammate at Airdrie and Dumbarton) were also footballers.[11][12]