Bobby Holloway is a 1965 graduate of Fyffe High School, where he played football, basketball, and baseball. He led the football team as quarterback and team captain and earned an All-County Honorable Mention in 1965. In basketball, he was the leading scorer and made the 1965 All-Sand Mountain Tournament and All-County teams. He was shortstop and pitcher of the baseball team, pitching a one-hit shut-out in 1965.
He later became a teacher and coach at Stevenson High School from 1979-1987, where he led the varsity girls basketball teams to two regional runner-up titles. He was also head coach of the junior high football team, assistant coach for the varsity football team, and head coach of the varsity baseball team. In 1989, moved to Valley Head High School, where he taught and coached varsity girls basketball, track, and volleyball until 2005. During his tenure at Valley Head, Holloway’s girls basketball teams won a DeKalb County Championship, a Super Eight championship, three regional championships, and two area championships. He also led the teams to three state Final Fours appearances.
Additionally, Holloway’s track teams won the state Bronze Medal in 1997 and the regional championship in 1999. He also led the volleyball team to the state playoffs in 1995.