The dynamic Bobby Saylor served as an assistant football coach under Hampden-Sydney Hall of Famer Stokeley Fulton, was the head tennis coach, and also served as an Assistant Athletic Director under Fulton. As a football player at The College, Saylor was an honorable mention All-America choice in 1961 at defensive end. Twice selected as his team's Most Valuable Player, Saylor was given the Virginia Small College Sportsmanship Award during his senior campaign. While a student at Hampden-Sydney, Saylor was a member of Chi Phi. On the coaching front, Saylor's 1972 tennis team captured the Mason Dixon championship. About a decade later, Saylor led Hampden-Sydney to its only two ODAC tennis titles in school history (1981, 1982), earning the distinction of ODAC Coach of the Year in both of those seasons. In 1983, Saylor was named Athletic Director and head football coach at Maryville College.