May joined the PGA Tour in 1994. He did not win on the Tour, but he finished second three times, including a playoff loss to Tiger Woods at the 2000 PGA Championship at Valhalla, and most recently at the 2006 B.C. Open at Turning Stone Resort & Casino, where he lost by one to John Rollins. However he won the 1999 Victor Chandler British Masters on the European Tour. His career was curtailed by a back injury in 2003, and in 2006 he played the PGA Tour on a Major Medical Exemption. After the 2007 season, he lost his PGA Tour card. From 2008 through 2010, May played primarily on the Nationwide Tour (now the Korn Ferry Tour) along with some PGA Tour events. He lost his status on the minor-league tour after missing 15 of 25 cuts in 2010; he played in only eight tournaments in 2011 and just twice in 2012.[4] May was in the top 50 of the Official World Golf Ranking for much of 2000 and 2001.