His first wife was actress Ellen Maud Pratt, the daughter of prosperous Devon farmer, John Dew Pratt of Buckland Monachorum. Her stage name was Judith Kyrle. They were married in Littleham-cum-Exmouth, Devon on 1 September 1894. Their careers reached a high point at their joint debut at the Britannia Theatre, Hoxton in April 1900 with Roy billed as "The Dramatic Cock o' the North". They had three children, John Kyrle born in 1895, Robin Roy (father of Major-General Sir Roy Redgrave) born in 1897 and Nellie Maud born in 1898.
