Bailey won promotion to the top flight with Wolves in 1966/67. 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.
He left Wolves upon winning the Second Division at the first attempt in 1977, moving to the NASL with the Minnesota Kicks for £15,000. He returned to England two years later to become player/manager of Hereford United in the Fourth Division. He served only one full season in the role, during which the club finished 14th, before leaving in October 1979.
He took up the reigns at former club Charlton 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. His one season in charge of the Seagulls brought them a highly credible 13th place in the top flight - their highest finish to date. He later also worked as a reserve team coach at Portsmouth until being sacked in 1995.
Bailey won 2 caps for England in 1964 during his Charlton days. He made his debut in a 10-0 demolition of the United States in New York on 27 May and also played against Wales in a 2-1 Home International win on 18 November.