5 =: Sir Matt Busby – 7
The legendary former Manchester United boss spent 25 year at the helm in his first stint at Old Trafford between 1945 and 1969, during which time the Scot brought home an impressive five top-flight crowns in 1952, 1956, 1957, 1965 and 1967, as well as two FA Cups in 1948 and 1963.