Career
Bailie began his career at Swindon Town, where he turned professional in 1982. He made his debut in the Third Division 5–0 defeat at Oxford United on 7 April 1982, playing as a full back. He made 121 appearances for the club in all competitions, scoring 4 goals, before a move to Reading in 1985 for a fee of £22,500.
While at Elm Park, he played a further 84 league games and played at Wembley as Reading reached the final of the Full Members Cup in 1986.
In 1992, Bailie claimed he had lost his appetite for football and was quitting the game. He had a brief spell in non-league football with Eynesbury Rovers before moving to Cumbria to become a police officer