Woodruff was a 21-year-old college freshman, an unsophisticated and, at 6 feet 3 inches (1.91 m), an ungainly runner.

During a career that was curtailed by World War II, Woodruff won one AAU (Amateur Athletic Union) title in 800 m in 1937 and won both 440 yd (400 m) and 880 yd (800 m) IC4A titles from 1937 to 1939.

Woodruff also held a share of the world 4×880 yd relay record while competing with the national team.

Woodruff graduated from the University of Pittsburgh in 1939, with a major in sociology.

While at the University of Pittsburgh Woodruff became a member of Alpha Phi Alpha fraternity.