Richard Gilliam began his career at Verbena High School in 1961 where he was the head football coach for five years. In 1965, he accepted the head coaching position at Calera for a seven year stint as their head coach before joining the Montevallo program in 1972 as an assistant football coach.

Gilliam became head coach at Montevallo High School in 1973 where he remained for the next fifteen seasons. His 1977 Bulldogs went 9-0-1 in the regular season before losing in the first round of the state playoffs. Gilliams record at Montevallo was 83-76-1 from 1973-1987.

Following the 1987 football season, Gilliam retired from the football field but not the classroom. He continued to teach for many years to come. In 2005 Gilliam retired from teaching and coaching at Briarwood Christian, where he spent 10 years helping coach the junior high boys football teams and girls basketball teams.

He was a well-respected coach for Montevallo High School. Coach Richard Gilliam was killed in an automobile crash on April 3, 2010. He was living in Clanton at the time of the crash.

Because of Gilliams contributions to the high school and the entire Montevallo community, Montevallo honored Gilliam by renaming their football field Richard Gilliam Field at Theron Fisher Stadium on Sept. 15, 2006 before the Bulldogs game against Marbury.