Cherry's first coaching position was at Ranger High School in Ranger, Texas, where he spent three seasons, from 1926 to 1928. In 1929, Cherry coached for one season at North Side High School in Fort Worth. In 1930, Cherry was named head coach at Amarillo High School. It was here that he established his reputation as a head coach. He compiled a record of 84 wins and 5 losses, with 45 of those wins by shutout. The average score in these games was 30–5. Amarillo High became the second school in Texas to win three straight state championships, in 1934, 1935, and 1936, allowing the opponent teams only a combined 13 points in these three championship games.
Cherry was considered as a candidate for the head coach position at the University of Texas at Austin in 1937, but was passed over for the better-known Dana X. Bible. Bible offered Cherry a position as an assistant coach on his staff. Bible groomed Cherry to be his successor, and upon Bible's retirement in 1946, Cherry was appointed as head coach. As head coach, Cherry switched the Longhorns' offense from a single-wing formation to the now-popular T formation, and found instant success. With Bobby Layne at quarterback, Texas earned a 10–1 record in his first year, a final ranking of fifth, and a defeat of sixth-ranked Alabama in the 1948 Sugar Bowl. In the 1948 season, his team compiled a 7–3–1 record and defeated eighth-ranked Georgia in the Orange Bowl. Following this season, Cherry was offered head coaching jobs by the Washington Redskins and Chicago Cardinals of the National Football League, but turned down these offers to remain the head coach at Texas. In 1949, Cherry's Longhorns compiled a 6–4 record. In 1950, the Longhorns won the Southwest Conference title with a 6–0 conference record, and earned a berth in the Cotton Bowl Classic, as well as a #3 final national ranking. Mid-season, Cherry announced that he would be retiring from coaching, and his last game was a 20–14 defeat at the hands of Tennessee in the 1951 Cotton Bowl Classic. Cherry was suffering from ulcers and insomnia at the time of his retirement, and later hinted in the article "Why I Quit Coaching" that harsh criticism from fans and media, despite his 32–10–1 record and two top-five finishes, led to his decision to retire.
Baseball
Cherry also served as baseball coach from 1943 to 1945 during Bibb Falk's absence. His teams compiled a 30–23 overall record, but won two conference titles with a 22–4 conference mark in three seasons. No SWC title was awarded in 1944.
Post-coaching life
After retiring from coaching, Cherry moved to Lubbock, Texas to enter the oil business. He died of heart failure in 1966, and is buried at Llano Cemetery in Amarillo. He was inducted into the Texas Sports Hall of Fame shortly before his death in 1966, and posthumously inducted into the Longhorn Hall of Honor in 1968.
