Lilyholm was born in Robbinsdale, Minnesota. Lilyholm graduated from the University of Minnesota in 1966 and played on the Minnesota Golden Gophers men's ice hockey team. As an amateur, he frequently played for the United States men's national ice hockey team.
Lilyholm was a member of Team USA at the 1968 Winter Olympics and the 1966, 1967, 1970, 1971, and 1974 Ice Hockey World Championships.
Outside hockey, Len Lilyholm was an architect and builder who participated in the design of the St. Paul Civic Center, the Saints' new home arena which was completed in January 1973. He appeared as a hockey coach in Ice Castles, a 1978 romantic drama film.

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