Bailey joined Charlton Athletic from non-League club Gorleston in 1958, and turned professional in March 1959.
He went on to play a central role during the club's resurgence of the Bill McGarry era, which saw the club reach the 1972 UEFA Cup Final and win the 1974 League Cup, where he lifted the trophy as captain, after a 2–1 win over Manchester City at Wembley.
[3][4] After Wolves won the Second Division at the first attempt in 1977,[3] Bailey moved to the North American Soccer League with the Minnesota Kicks for £15,000.
He took up the reins at former club Charlton Athletic in March 1980 and guided them to promotion from the Third Division at the first attempt in 1980–81 before moving to Brighton & Hove Albion.
[1] He made his debut in a 10–0 demolition of the United States in New York's Downing Stadium on 27 May 1964,[6] and also played against Wales in a 2–1 Home International win on 18 November the same year.