Dillon was born on January 14, 1887, in Normal, Illinois.[1] He graduated from high school in Normal in 1905 and then attended Illinois State Normal University—now known as Illinois State University—also located in Normal. He played football at Illinois State Normal from 1905 to 1907 as a halfback and captained the 1907 team.[2] In March 1907, Dillon was hired as a teacher of literature and Latin and track coach at the University of Middle Tennessee, located in Tullahoma, Tennessee. He returned to Illinois State Normal that fall to complete his studies and captain the football team.[3]
Dillon went to the University of Illinois in 1909 and was elected captain of the freshmen football team. He played for three seasons, from 1910 to 1912, for the Illinois varsity football team at halfback before graduating in 1913.[2]
In 1919, Dillon was hired as athletic director and coach at Howard College—now known as Samford University—in Birmingham, Alabama.[5] A year later, he left Howard to take on the same role at Oshkosh State Normal School—now known as University of Wisconsin–Oshkosh.[6] From 1921 to 1924, Dillon was the athletic director and coach for the city schools in Coffeyville, Kansas.[7] In 1925, he returned to Howard College as athletic director.[8] He served as the backfield coach for 1925 Howard Bulldogs football team, assisting head coach Jenks Gillem. In 1926, Dillon coached the freshmen football team before resuming the role of head coach of the varsity football team in 1927.[9]
