He led the school to two consecutive state football championships and was unanimously selected as an all-state halfback both years.

In the Harvard game, played in Cambridge, Massachusetts, Bennett accounted for Indiana's only points on a 30-yard touchdown run.

Indiana had never beaten Michigan, but Bennett played all 60 minutes of the game, and his long runs helped lead the Hoosiers to their first win against the Wolverines—by a 6–0 score.

Bennett scored Indiana's only touchdown in the Illinois game on a 24-yard run, completed several forward passes and had the Hoosiers at Illini two-yard line when time ran out.

[2] He was also a popular student on the Bloomington campus, where he was elected president of the junior class and was a member of Delta Upsilon fraternity and the Sphinx Club, an honorary organization.

[1] In June 1929, Bennett signed a contract to play professional football for the Portsmouth Spartans, predecessor of the Detroit Lions.

In May 1937, he accepted a position as football coach and athletic director at the high school in Austin, Minnesota, where he remained for two years.

[8] In 1939, Bennett was hired as a football coach and athletic director at Lyons Township High School in La Grange, Illinois.

[9][10] He coached the Lyons Township football team for 21 years and won 11 West Suburban Conference championships.

[11] In 1958, the Chicago Tribune credited Bennett with turning the school into an athletic power: "In his 20th year as athletic director and football coach at Lyons Township High school in La Grange, Chuck Bennett can point with pride to a truly impressive record -- certainly one of the best in the Chicago area prep field.

"[12] Bennett resigned as head football coach in 1960 but continued to serve as the school's athletic director.

[13] On 20 occasions, Bennett won the President's Cup at Lyons Township, awarded for overall sports supremacy in the West Suburban Conference.