Donnie Chesteen is a native of Hartford and a graduate of Geneva County High School. During his high school days, Chesteen lettered in football, basketball, baseball and track. He was a standout on the football field, playing quarterback for the Bulldogs for three seasons. In 1988, he was selected to the All-Time Geneva County High Football Team.

Following high school, he graduated from Troy State in 1975. He landed his first coaching job as an assistant football coach at Geneva High under Coach Max Griffin that same fall. Chesteen returned to Geneva County, his alma mater, as a 24-year-old head football coach and athletic director in 1977.

Geneva County won the Wiregrass Athletic Conference championship in 1979 and Chesteen was named WAC Coach of the Year. He led the Bulldogs to the playoffs for the first time in school history.

In 1981, Chesteen was hired at Geneva High School as the head football coach and athletic director. He led the Panthers to seven consecutive winning seasons from 1981 through the 1987 football season. He also led Geneva to the state playoffs for the first time in school history. His best team with the Panthers came in 1986 when they finished with a 11-2 slate.

His overall record as the coach of the Panthers is 72-40. He came out of retirement to take over the football program at Samson in 2010 where he stayed for two seasons before returning to Geneva in 2012. In 16 years as a head football coach, Chesteen compiled a mark of 99-74 before retiring following the 2014 season.

Chesteen was inducted into the Wiregrass Hall of Fame in 2002. He joined his father, J.D. Chesteen, who had been elected years earlier.