Cummiskey was born in England and moved to South Africa in 1969 with his family for a few years and he returned in 1983 as an adult.
[1] He is the founder and editor of Dye Hard Press, which, since 1994, has published writers such as Khulile Nxumalo, Gail Dendy, Arja Salafranca, Alan Finlay, Philip Zhuwao, Roy Blumenthal, Gus Ferguson, Kobus Moolman, Pravasan Pillay, Graeme Feltham and Allan Kolski Horwitz.
Also in 2009, Cummiskey compiled Beauty Came Grovelling Forward, a selection of South African poetry and prose published online at www.bigbridge.org.
Through Dye Hard Press, Cummiskey published an anthology of South African short fiction, The Edge of Things, selected by Arja Salafranca, in 2011.
From 2014 to 2016 he was editor of the South African poetry journal New Coin, which is published by the Institute for the Study of English in Africa, at Rhodes University, Grahamstown.