He is the namesake of the Outland Trophy, an annual award established in 1946 and given to the best interior lineman in college football.

Outland worked his way through college and spent his last two summers as a companion to rich young men who were alcoholics.

[4] In 1900, Outland coached the football team at Franklin & Marshall College in Lancaster, Pennsylvania for one season.

[8] The 1902 Haskell Indians football team compiled a record 8–2–1 with victories over Missouri, Texas, and Kansas.

[10] Outland's 1905 season ended with an experimental game with Fairmount, where a new rule forcing the offense to earn a first down in three plays instead of four was in effect.

[11] In 1906, Outland returned as head coach of the Haskell Indian Nations football team in Lawrence.

Later, in about 1916, while still on staff with Trinity-Lutheran hospital he moved his family across state lines to Kansas City, Missouri[14][15] 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.

[18][19] 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.