Derby first appears in September 1381 as one of the witnesses to a deed regarding land in Bermondsey, this being the first of five occasions on which he is known to have discharged such a function.
Meanwhile, in July of that year, Derby and two other local men obtained the reversion of two tenements in Bermondsey from Henry Boghay, the rector of St. Olave’s church, Southwark. It was about this time that he himself came before Chancery as one of the four plaintiffs in a suit for the ownership of a hostelry called The Dragon on the Hope in Bishopsgate. He was probably also the William Derby named, in November 1410, among the 11 merchants and tradesmen against whom William Skrene had filed a plea of intrusion in the court of the mayor of London. This concerned houses in a number of city parishes, but the outcome remains unknown.
