Although born in England, Bailey grew up in South Africa and started his career with
Wits University in Johannesburg. In the late 1970s, Bailey paid his own fare to Manchester for a trial with
Manchester United. He made his debut against Ipswich Town (who his father,
Roy Bailey, had played for, and also his birthplace), on 18 November 1978. He went on to play 294 games for the Red Devils between 1978 and 1987. He established himself as United goalkeeper in the late 1970s following the retirement of
Alex Stepney. He was considered to be one of the best goalkeepers in England in the early to mid-1980s. During his time with Manchester United, Bailey won
FA Cup medals in
1983 and
1985. He played under three United managers:
Dave Sexton,
Ron Atkinson, and
Alex Ferguson. He represented the
England national team twice at senior level, but was unable to establish himself in the first XI due to the form of the more-experienced
Peter Shilton and
Ray Clemence. He was first capped against the
Republic of Ireland on 26 March 1985, won by England 2–1, with his other international appearance coming on 9 June that year in a 1–0 loss against
Mexico. However, he developed a serious knee injury during training at the
1986 FIFA World Cup and missed most of the
1986–87 season, after which he retired and returned to South Africa. He subsequently resumed his career with
Kaizer Chiefs in 1988, winning a quadruple in 1989 before retiring in 1990.
Peter Schmeichel said on
BBC Match of the Day 3 that Gary Bailey was his favourite goalkeeper of all time and he idolised him as a youngster growing up in Denmark. ==Post-playing career==