Dillie was the head coach of the Mississippi Normalcollege football program in Hattiesburg, Mississippi (now called "University of Southern Mississippi"). He held the position from 1914 until conclusion of the 1916 season and was the third person to hold the position at the school. His overall record at Southern Miss was 6 wins, 10 losses, and 1 tie. As of conclusion of the 2009 season, this ranks him 12th in terms of total wins at the school.
A unique positive turning point occurred in the 1916 season as the result of a loss. In what was called the program's "Greatest pre-World War I success" the team lost to Ole Miss by a score of 13 to 7. The school's leadership at the time took this as a sign that the program could compete nationally in the sport of football.
Due to World War I, the school ceased competing in football after completion of the 1916 season and did not restart the program until 1919, when Cephus Anderson would start the program back up.
While at Mississippi Normal, Dillie also served as the head basketball coach from 1913 until the conclusion of the 1915-1916 season, where his teams produced a record of 29 wins and 14 losses (0.674). Dillie was the second person to hold the position at the school.