Derrick May, a left-handed outfielder and first baseman, embarked on his Major League Baseball journey when he was drafted by the Chicago Cubs in the first round of the 1986 MLB Draft. His professional debut came in 1990 with the Cubs, where he began to establish himself as a reliable player. May's early years with the Cubs saw him gradually gaining more playing time, and by 1992, he had become a regular in the lineup. That year, he posted a .271 batting average with 8 home runs and 50 RBIs, showcasing his potential as a solid hitter.

In 1993, May had one of his best seasons with the Cubs, achieving a .295 batting average, hitting 10 home runs, and driving in 77 runs. His performance that year demonstrated his ability to contribute offensively, and he became a valuable asset to the team. However, his time with the Cubs came to an end after the 1994 season when he was traded to the Milwaukee Brewers.

May's stint with the Brewers was brief, as he played only one season with the team in 1995. During that year, he struggled to find his form, hitting .234 with 5 home runs and 35 RBIs. Following his time in Milwaukee, May signed with the Houston Astros, where he played for two seasons. In Houston, he found a bit more success, particularly in 1996 when he hit .292 with 8 home runs and 42 RBIs.

After his tenure with the Astros, May's career took him to the Philadelphia Phillies in 1997. His time in Philadelphia was marked by a decline in his offensive production, as he hit .230 with 5 home runs and 33 RBIs over two seasons. In 1999, May joined the Montreal Expos, where he played his final season in the major leagues. That year, he managed a .274 batting average with 3 home runs and 20 RBIs.

Throughout his career, Derrick May was known for his steady presence in the outfield and at first base. While he may not have been a standout star, he provided consistent performances and contributed to the teams he played for.