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.