Webb was a two-time All-Conference offensive lineman and linebacker for Olive Branch, where he played varsity football for the Quistors under former head coach Leslie Pool and helped OBHS capture the runner-up spot in the old Chickasaw Conference in back-to-back years (1976 and 1977) and a Conference Co-Championship Title in the 1978 season. 

He was  selected for First Team All-Chickasaw Conference honors in both his junior and senior seasons (1977 & 1978) as both an offensive guard and linebacker, and was also selected as the Conference's Most Valuable Player as an offensive lineman his senior year.

After graduating from OBHS in 1979, Webb attended Jackson State University, where he played as a linebacker for the Tigers.  He could be found on the gridiron the past number of years officiating football games for the Mississippi High School Activities Association and in the SWAC Conference on the collegiate level.