Dille starred at Chesterton High School in Chesterton, Indiana and matriculated at Valparaiso University as a 26-year-old with a wife and son. He played varsity basketball while working 48 hours a week at a local company in addition to his full courseload. In 1944, Dille was named Valparaiso's first nationally recognized All-American.
Dille later coached high school basketball in his home state of Indiana. He coached at Valparaiso High School, Berne-French Township High School and Fort Wayne North before taking the reins at Fort Wayne Northrop in 1971. Dille coached at Northrop for seven years, winning a state championship in 1974.