The Northern Irishman broke on to the scene with Manchester United after coming through the club's youth system but really made his name in England with Newcastle United and then Blackburn Rovers.
He best years were perhaps behind him when he joined Leicester from Blackburn in 2003. He signed on a free transfer and played 48 games for the club, scoring two goals in two seasons. Jet-heeled, what he lacked in finishing he made up for with his pace on the wing.
Unfortunately, off the field Gillespie was one of three City players - alongside Frank Sinclair and Paul Dickov, who spent a week in a Spanish jail after being accused of sex offences at La Manga. The charges were later dropped but they had a stain on Gillespie's time at the club.
He left for Sheffield United in August 2005 and went on to play for Bradford City, Glentoran, Darlington and Longford Town.