Career
He played as a midfielder and full back for several clubs, including Hibernian, Falkirk and Motherwell during the 1980s and 1990s. When he joined Brentford in July 1989, May"s £167,000 transfer fee was a then-club record. After retiring as a player, May became a coach, developing young players for Falkirk.
May was appointed as the manager of Falkirk in June 2009, with former player Steven Pressley and Alex Smith assisting him.
His first competitive game was a 1–0 victory over Football Club Vaduz in the Union of European Football Associations 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. May developed a reputation for being brutally honest during his spell in charge at Falkirk.
May resigned as Falkirk manager soon afterwards, however, with the team bottom of the SPL. May returned to football in June 2010, becoming a youth coach with Rangers. He was appointed high performance coach at the University of Stirling in August 2012.
May returned to Hibernian in August 2014 when he became their academy coaching manager.