Shipley graduated from the Maryland Agricultural College (now the University of Maryland) in 1914. While there, he played basketball, baseball, and football as a quarterback. In 1923, he became the head coach for the Maryland basketball team, a position in which he would serve until 1947. During his tenure, he compiled a 243–199 record. Also in 1923, Shipley was hired as an assistant coach for the football team under legendary Maryland head coach Curley Byrd. Shipley also coached the baseball team from 1924 to 1960.