He is said to have been in the service of Queen Elizabeth by 1563, obtained 'commendation for his learning and eloquence' in a public disputation before her on 3 September 1566 at the University of Oxford,[7] and was appointed as her secretary for the Latin tongue after the death of Roger Ascham on 30 December 1568 in preference to Bartholomew Clerke, who had the support of the Earl of Leicester, Sir William Cecil and Walter Haddon.
[6] On 24 July 1573 Wolley corresponded with the German scholar, Johannes Sturm on the controversial topic of the vestments to be worn by the clergy of the Church of England,[9] stating that he was doing so 'at the desire of my singular good patron, the Earl of Leicester'.
On 18 July 1591, together with his fellow councillor, Sir John Fortescue, he conducted the initial examination of the religious fanatic, William Hacket.
[16] Wolley was knighted in 1592,[17] and in November of that year was one of those appointed to investigate John Dee's complaint that his service to the Queen had not been properly recognized and compensated.
[14] On 20 October 1595, after the death of Sir Thomas Heneage, Wolley made suit to the Queen to be appointed Chancellor of the Duchy of Lancaster, stating that he had served her ‘now upon the point of 30 years’.
[18] Wolley's literary interests and literary patronage are suggested by verses he composed for Joannis Juelli Angli … vita et mors (1573) by Laurence Humphrey, and by several books dedicated to him, including A Pleasant Description of the Fortunate Ilandes, called the Ilands of Canaria (1583) by T. Nicholas, Churchyards Challenge (1593) and A Revyving of the Deade (1591) by Thomas Churchyard, and Diarium historicopoeticum (1595) by Robert Moor.
[21] In 1614 the bodies of Wolley, his wife, Elizabeth, and son, Sir Francis, were reburied ‘between St. George's Chappel and that of our Lady’, and a magnificent monument was erected to their memories at a cost of £4000.