Career
He made one appearance for Hibernian in the Premier Division, but was then released. Bailey then went on to play for Meadowbank and stayed with the club when it relocated to Livingston. He was playing for Brechin City, a part-time club, when they were drawn to play Rangers in the 2000-2001 Scottish Cup.
Bailey was also working as a driving instructor at that time.
In June 2015, Bailey was appointed assistant manager of Brechin City. At that time, Bailey was also working for the Fife Football Performance Academy.
