He came of an old Yorkshire family of some substance and was apprenticed to John Reynes, who is best known as a bookbinder and who died in 1543 or 1544.
per annum, Cawood was directed to print all "statute books, acts, proclamations, injunctions, and other volumes and things, under what name or title soever" in English, with the profit appertaining.
He was also granted the reversion of Reyner Wolfe's patent, authorized in 1547, for printing Latin, Greek and Hebrew books, for which he was to receive an additional 16s.
In 1553 Cawood seems to have acquired a certain amount of printing material from Steven Mierdman, who on the accession of Mary had been obliged to leave England.
As Queen's Printer to Mary, Cawood was responsible for printing the proclamations and acts published during her reign, but on the accession of Elizabeth, the proclamation to that effect was printed by Richard Jugge, who subsequently printed several others and was termed in a letter from the Privy Council dated 20 December 1558, "the Quenes Majesties Prynter."