He played as a midfielder and full back for several clubs, including Hibernian, Falkirk and Motherwell during the 1980s and 1990s.
[5] May was appointed as the manager of Falkirk in June 2009, with former player Steven Pressley and Alex Smith assisting him.
[5][6] His first competitive game was a 1–0 victory over FC Vaduz in the UEFA Europa League qualifying rounds, although Falkirk eventually lost their first ever European tie 2–1 on aggregate, becoming the first British club to lose a European tie to a club from Liechtenstein.
[12] He was put in caretaker charge of the Hibernian first team in January 2019, after Neil Lennon was suspended by the club.
May appeared for a brief goal in Rangers colours in the movie A Shot at Glory which also starred Robert Duvall, Ally McCoist, Brian Cox, Michael Keaton and Owen Coyle.