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Clifford began writing poetry at fourteen. His first collection, Man in a Window (1965), was the first volume published by Canadian literary publisher, Coach House Press. As a student at the University of Toronto (BA 1967), he shared the E.J.Pratt Prize with Michael Ondaatje. He attended the University of Iowa's International Writers' workshop (MA 1969, MFA 1969), where he worked with Harry Duncan of Cummington Press, and founded Living Series, which published work by colleagues as broadsheets and chapbooks (Michael Lally and Ray DiPalma, among others). Although he was invited as a delegate to the founding conference of the League of Canadian Poets, and helped organize the Kingston's Writers' Association, the Kingston branch of Canadian Artists' Representation, and The Monday Night Boys, Clifford has never allied himself with a school, group or faction. His work demonstrates this independence, moving between elegant, dense and often highly musical freer compositions to an unfashionable but exquisitely made formalism. Clifford has published in a broad range of journals, from The Canadian Forum, Queen's Quarterly and ARC to avant-garde magazines like bill bisset's Blewointment, bpNichols's ganglia, and Sheila Watson's Pelican.
- Man in a Window. Toronto: Coach House, 1965.
- Eighteen. Toronto: Coach House, 1966.
- Alphabook. Kingston, ON: MakeWork, 1972.
- Glass.Passages. Ottawa, ON: Oberon, 1976.
- An Ache in the Ear. Toronto, ON: Coach House, 1979.
- On Abducting the 'Cello. Erin, ON: Porcupine's Quill, 2004.
- The Book of Were. Erin, ON: Porcupine's Quill, 2006.
- The Exile's Papers: The Duplicity of Autobiography, Part One. Erin, ON: Porcupine's Quill, 2007.
- The Exile's Papers: The Face as its Thousand Ships, Part Two. Erin, ON: Porcupine's Quill, 2009.
- Jane Again. Emeryville, ON: Biblioasis, 2009.
- Learning to Dance with a Peg Leg. Victoria, BC: Frog Hollow Press, 2009.
- The Exile's Papers: The Dirt's Passion Is Flesh Sorrow, Part Three. Erin, ON: Porcupine's Quill, 2011.
- b.p. Nichol & Wayne Clifford, Theseus: A Collaboration. Toronto, ON: BookThug, 2014.
- The Exile's Papers: Just Beneath Your Skin, The Dark Begins, Part Four. Erin, ON, Porcupine's Quill, 2016.
- Reid, Diane (3 October 2009). "Poetry collection 'is more jig, swing, stomp, and swivel than intimate waltz'". The Daily Gleaner. Retrieved 6 October 2010.