After receiving his medical degree, Outland returned to Kansas in 1900 where he set up his medical practice first in
Lawrence, Kansas which led to his hiring as the head football coach of the University of Kansas. On January 28, 1902 Outland married Ethel Arnett Grimes in her hometown of
Dana, Indiana. He then moved his practice to
Topeka, Kansas in 1904 in order to coach the Washburn University football team. In 1906 Outland moved his family to
Kansas City, Kansas where he joined the very first staff of the brand new Trinity-Lutheran hospital in
Kansas City, Missouri as a general practicing surgeon. Later, in about 1916, while still on staff with Trinity-Lutheran hospital he moved his family across state lines to Kansas City, Missouri where he lived until his retirement. During his time as a practicing surgeon he extensively used his own plane, often flying with famous Kansas City early aviation pioneer pilot John Kerr "Tex" LaGrone, to visit patients in rural areas and far flung towns, being the first doctor in the Kansas City area to do so. While practicing medicine in the Kansas City region, Dr. Outland served for many years on the athletic board of the University of Kansas alongside other notable KU alumni,
Dr. James Naismith and
Dr. Forrest "Phog" Allen amongst others. Dr. Outland also served as a referee for college football games, including the 1907 Iowa State - Nebraska game in which he rendered the decision that negated an Iowa State field goal and preserved a
10-9 Nebraska victory. Upon his retirement he moved to Laguna Beach, California. He also served as a
major in the
United States Army Medical Corps during
World War I.
Kansas Relays Outland was the founder of the
Kansas Relays, having obtained the inspiration for that event at Penn, when as a student, he saw the
Penn Relays just getting under way. For many years he held the post of honorary referee of the Kansas events. He was survived by his wife, Ethel, daughter Mrs. Mary McDougall of
New Orleans, Louisiana, and son John Grimes Outland of
Dallas, Texas. Outland was laid to rest in Maple Grove Cemetery in
Wichita, Kansas near his parents' graves. ==Head coaching record==