Sir Roger Hillary was an English judge. He was one of five sons of William Hillary and his wife Agnes, a landowning family which held properties in Lincolnshire, Warwickshire, Staffordshire, and Leicestershire, and appear to have been related to Sir William Bereford, the Chief Justice of the Common Pleas; a useful connection for a nascent lawyer. In 1310 Hillary was recorded as a court attorney, and in 1324 he was made a Serjeant-at-law. In the later years of Edward II's reign Hillary kept a low profile. In spring 1320 he married Katherine, and added to his property portfolio the Manor of Fisherwick near Lichfield in 1327 and a life-grant of a mill at Bentley at around the same time.