Charlie Gregory compiled an impressive coaching record in a number of sports at Randleman High School. Gregory is probably best known for developing Randleman into a football powerhouse. He coached that sport 28 years, winning over 200 games, and earned three consecutive NCHSAA state 2-A football titles, from 1981 through ’83. He served as Randleman’s athletic director for 18 years but also coached basketball, track and golf during his stint there. He coached in the North Carolina Coaches’ Association East-West football all-star game in 1974 and the Randleman High football stadium is named in his honor. A graduate of High Point College, Gregory was a three-sport star at Trinity High School and played on the 1949 state basketball championship team. He is also a charter member of the Randleman Civitan Club.