|Date of birth||26 September 1958|
|Place of birth||Wigan, England|
|1986–1987||→ Newport County (loan)||9||(1)|
|* Senior club appearances and goals counted for the domestic league only.
He began his career at Newport County in the early 1980s, during the most successful period in the club's history. Bailey was part of the team that won promotion and the Welsh Cup and, in the subsequent season, reached the quarter-finals of the 1980–81 European Cup Winners' Cup. Bailey made 134 appearances for Newport, scoring seven goals.
In 1986, Bailey joined Stockport County and went on to make a half-century of appearances for the Greater Manchester club. During his time at Edgeley Park, he was loaned out to his first club, Newport County.
Bailey retired from playing in 1988, but stayed on at Stockport County as a coach.
In January 2007 Roy Keane was appointed team manager of Sunderland and he appointed Bailey as first team coach. When Keane resigned in December 2008 Bailey was promoted to joint Assistant Manager with Dwight Yorke under caretaker manager Ricky Sbragia. Steve Bruce was appointed Sunderland manager in July 2009 with Sbraglia and Bailey subsequently being released by Sunderland.
In 2010 Bailey rejoined the PFA as a Regional Coach Educator in North West England.