Eyland was a curator at the Technical University of Nova Scotia School of Architecture (Daltech) and freelanced for the Plug In Institute of Contemporary Art in Winnipeg. From 1995 to 2005, Eyland was vice-president of the board of Plug In. In 1998 he was hired as an associate professor of painting at the University of Manitoba School of Art and was also director of Gallery One One One, both positions he held until 2010.Eyland was represented by Gurevich Fine Art in Winnipeg. His work is held at the University of Manitoba Archives & Special Collections. In 2020, his alma mater, Nova Scotia College of Art and Design, has set up the "Cliff Eyland Memorial Scholarship" for painting students and endowed by his family.