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He has written two books – Success under Pressure, with the foreword written by former manager Sir Alex Ferguson, and a personal book to help society on divorce called "Putting the Kids first".

He was an ambassador in South Africa's successful bid to host the 2010 FIFA World Cup.

Besides being a TV soccer expert, he was also a top keynote speaker on the subject of "Success under Pressure" and travelled the world speaking to many of the top companies such as Microsoft, IBM, Nike, Coca-Cola, Mercedes Benz and many more. He was recognized for his speaking success by being inducted into the Speakers Hall of Fame in 2010.

He met his current wife Michelle Mclean (Miss Universe 1992) in 2010, married in March 2013, and then emigrated in December 2013 to USA and currently lives on Miami Beach in Florida.

After retiring in the UK, Gary Bailey returned to South Africa, and after resting his knee, decided to return to play for glamour club Kaizer Chiefs with whom he won the league in 1989 and amassed five trophies in two years.

On returning to South Africa in 1987, Bailey married Kate Saunders in 1990 and had three children, Lara, Jenna and Ross. They couple divorced in 2006.

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 where he subsequently resumed his career with Kaizer Chiefs, before retiring in 1990.

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.

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), on 18 November 1978. He went on to play 294 games for the Red Devils between 1978-1987.

The 6' 2" player 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 the reigns of the following Manchester United managers: Ron Atkinson, Dave Sexton, and Alex Ferguson.

Gary Richard Bailey (born 9 August 1958) is a former footballer who made nearly 300 appearances in the Football League playing as a goalkeeper for Manchester United. Born in Ipswich, Suffolk, he grew up in South Africa, but went on to be capped twice for England.