Little attended Ohio State University as an agriculture student. While there, he also served as an assistant coach for the 1912 and 1913 Ohio State Buckeyes football teams. He was "given credit for lending much help" to John Wilce in leading the 1912 Ohio State team to an Ohio Athletic Conference championship. The success of the 1912 team led to Ohio State's admission to the Big Ten Conference for the 1913 season. Cincinnati In January 1914, Little was hired as the head football coach at University of Cincinnati. During the 1914 season, Little led Cincinnati to a 6–3 record, as his team shut out five opponents and outscored all opponents, 164 to 44. In 1915, his team compiled a 4–5 record and was outscored, 158 to 110. Miami In January 1916, Little was hired as the head football coach at Miami University in Oxford, Ohio, succeeding Chester J. Roberts. During the 1916 season, Little led Miami to a 7–0–1 record and an Ohio Athletic Conference championship. This team shut out six of eight opponents and outscored all opponents by a combined total of 238 to 12. The only blemish on the record of the 1916 team as a scoreless tie with Denison. Little's tenure was interrupted by his service in the armed forces during World War I. He served as a captain in the infantry from August 15, 1917, to August 7, 1918. He returned and led the Redskins a 7–1 record in 1919 and a 5–2–1 record in 1920. He once again won the Ohio Athletic Conference championship in 1921 with a perfect 8–0 record. The 1921 team scored 238 points during the season and gave up only 13. In his four years as Miami's head coach, Little compiled a record of 27–3–2 including 21 games where the opponent did not score. He left Miami to become Fielding H. Yost's top assistant at the University of Michigan. Michigan In May 1922, Little was hired by the University of Michigan as assistant athletic director and assistant football coach. Little was the top assistant under Fielding H. Yost for the 1922 and 1923 seasons before being named head coach for the 1924 season. That year, he compiled a record of 6–2. Little and the Wolverines shut out their opponents in five of the six victories. Wisconsin In January 1925, Little accepted an offer from the University of Wisconsin to become its