In the fall of 1895, John Outland entered the University of Kansas. He had previously played football for two seasons and had been team captain at William Penn in Iowa. While watching practice one afternoon at Kansas, he was seen by the varsity captain who induced him to put on a uniform. Three days later, he was playing on the varsity team. After a 6–1 season, he transferred to the University of Pennsylvania where he found his home. From 1897–99, Outland and Hall of Fame teammate Truxton Hare led Penn to a 35–4–3 record. Outland obtained his medical degree and was a surgeon during World War I, rising to the rank of major. He tried his hand at coaching at Franklin & Marshall College in 1900, Kansas in 1901, and Washburn 1904–05.