May batted left-handed and threw right-handed. After signing to play football/baseball at Virginia Tech. May was drafted in the first round (#9) of the 1986 June draft by the Chicago Cubs at the age of 17. May hit .320 (3rd), .298 (11th), .305 (5th), .295 (5th), and .296 (5th) including being a Carolina League and Southern League All-Star before making his Major League debut. May enjoyed an 18-year professional baseball career including ten seasons in the MLB. He was a .271 hitter with 52 home runs and 310 RBI in 797 Major League games played. In Japan, he hit an additional 59 home runs in just three seasons, batting .274.
Derrick May is the son of the late major league outfielder Dave May. His brother, David May, Jr., is a scout for the Toronto Blue Jays.
May has been working as a hitting coach in the St.Louis Cardinals Organization since 2005.
2005: Coached the Palm Beach Cardinals (High A) to the Florida State League Championship his first year in 2005.
2006: Won both halves and made playoffs in the Florida State League.
2007: Promoted to (Double A) Springfield, Mo. of the Texas League. Coached them to the Texas League championship finals and his team led the league in hitting (.271), hits and OBP (.345) 2nd in runs scored, HR's, SLG (.431) and OPS (.776).
2008: Coached Springfield to the 2nd best record in the league. The team batted .275, first in HR and tied for 2nd in hits and TB(Total bases).
2009: Won the first half in Northern division. Lost in the first round of the playoffs. His team Led the league in HR's and tied for 2nd in 3b's. 2010: Was the Springfield hitting coach that finished with the 2nd best record in the league at 76–64. His team finished tied for 2nd in batting at .264, 1st in HR's with 146, 2nd in 2b's, runs scored, total bases, bb's, OBP,SLG and OPS.
Has served as the Minor League Hitting Coordinator for the 2011 and 2012 seasons.