He played guard at the University of Pennsylvania under his older brother, George Washington Woodruff.

His family moved to Tecumseh, Nebraska from Friendsville, Pennsylvania in 1865 where his father was a dry goods dealer.

Sometime after February 1868 his family moved back east briefly to Binghamton, New York and then to his mother's hometown of Friendsville, Pennsylvania where Woodruff spent most of his childhood.

The 1880 Census has him living with Dr. Henry P. and Sarah E. née Glidden Hasting (his mother's sister) at Culver Township, Ottawa County, Kansas.

Woodruff played football for the University of Pennsylvania from 1893 through 1896 while studying to receive his medical degree.

[5] When he first arrived at Kansas, he moved in with the players in their training quarters and enforced strict codes of conduct.

[3] He was the fourth head football coach for the University of Kansas and he held that position for two seasons, from 1897 until 1898.

[7][8] Upon his departure as head football coach at Kansas, Woodruff set up practice as a physician in Lawrence, opening an office at 709 Massachusetts Street in January 1898.

[12] He soon returned to Lawrence, Kansas and announced he had consumption, known today as Tuberculosis, which required him to move west to a drier climate.

Upon arrival in Portland, he again set up his medical practice, this time specializing in gynecology, obstetrics, and abdominal surgery.

He was survived by his wife, Edith I. Woodruff (née Green), daughter Mrs. Cormella Glidden Yenney (1904 – April 30, 1950), son George Walter Woodruff (November 8, 1906 – October 6, 1987), and grandson George Wylie Yenney (May 23, 1926 – November 16, 1994).