McCutchan spent seven years coaching Benjamin Bosse High School (1936–1943) before serving in the United States Navy during World War II.

In the following years he guided them to five NCAA College Division Basketball Championships (1959, 1960, 1964, 1965, 1971) and three undefeated seasons in their conference (1964, 1965, 1971).

McCutchan was named NCAA College Division Coach of the Year two times (1964, 1965).

He was an assistant coach to Gene Bartow for the US national team in the 1974 FIBA World Championship, where he won the bronze medal.

[3] After retiring from coaching, he and his wife Virginia moved to Santa Claus, Indiana.