Clifford Leslie Joseph Eyland was born November 7, 1954 to Kathleen Margaret Eyland (nee Williams) and Ronald James Eyland in Halifax, Nova Scotia. Eyland studied at Holland College, Mount Allison University, followed by the Nova Scotia College of Art and Design (NSCAD).

In the 1980s, Eyland began making paintings, drawings and notes in a 3”x5” index card format. Since then, much of Eyland’s work has explored the relationship between libraries and galleries, both of which are institutions that house and preserve. Eyland’s index card project has formed some of his largest installations which appear in libraries across Canada, such as Winnipeg’s Millennium Library, the Halifax Central Library and Edmonton’s Meadow Library. In addition to his large-scale library installations, Eyland has had several solo exhibitions and participated in many group shows throughout North America and Europe. In 2003, he was shortlisted for the nation RBC/Canadian Art Foundation painting award.

Eyland’s writing has been published in Canadian art magazines since 1983, and Eyland has been curating exhibitions since 1985. He served as a curator at the Technical University of Nova Scotia School of Architecture (now known as Daltech) from 1985 until 1994. In 1998, Eyland became the Director of Gallery One One One (now known as the School of Art Gallery), where he would remain until 2012. During this time, Eyland also taught at the University of Manitoba and served as a board member on Plug In ICA’s Board of Directors from 1995 until 2005.