Bailey made 151 league appearances for Charlton Athletic and became club captain before joining Wolverhampton Wanderers in March 1966 for a fee of £40,000.
He quickly became an important figure at Molineux, helping Wolves win promotion to the First Division in 1967. Under Bill McGarry, the club enjoyed a memorable revival, reaching the 1972 UEFA Cup Final.
Two years later, Bailey captained Wolves to League Cup glory, lifting the trophy at Wembley following a 2–1 victory over Manchester City.
After Wolves won the Second Division in 1977, Bailey moved to the Minnesota Kicks before returning to England as player-manager of Hereford United in the summer of 1978.
The Bulls had suffered back-to-back relegations into what is now League Two, and Bailey guided the club to a 14th-place finish in his first season. He also made 16 league appearances, scoring once.
Bailey left Edgar Street in October 1979, returning to Charlton Athletic as manager. He immediately made an impact, guiding the club to promotion from the Third Division at the first attempt.
He later managed Brighton & Hove Albion, leading the Seagulls to what was then their highest-ever league finish, 13th in the First Division.
He was diagnosed with dementia in late 2020.
