Born in Columbus, Georgia in 1889, Woodruff attended Columbus High School and the University School for Boys in Stone Mountain, Georgia before enrolling at the University of Georgia in Athens in 1907. He played quarterback for the Georgia Bulldogs football team during the 1907 and 1908 seasons before taking a year off from school to travel around the United States and Mexico. After returning to the university and rejoining the football team in 1910 and 1911, when he was team captain, Woodruff graduated with a Bachelor of Arts degree in 1912.