Wolley traded as a draper in Derby. Following his marriage he became involved in litigation in the court of common pleas over the wardship and estates of his stepson, William Ireland, first with the widow of Sir Robert Francis and then, in 1426, with John Merbury. Although a local jury found against him in the first instance, awarding £35 damages to Isabel Francis, and Merbury also apparently secured a favourable verdict, our MP was none the less recorded as in possession of the disputed manor of Hartshorn in 1428 and 1431.
At the sessions of the peace held at Derby in 1426, Wolley stood surety for members of the Colman family and served as a juror in the suit between Ralph Hussey and Thomas Dethick. He later, in 1430, acted in the same capacity when Robert Eyre of Padley, ‘gentleman’, was tried for murder before the justices of gaol delivery. He attended the borough elections to the Parliaments of 1429 and 1433.
