In 1553 Wolley became a
Fellow of
Merton College, Oxford. He was granted the degrees of
Bachelor of Arts on 11 October 1553,
Master of Arts on 1 July 1557, and
Doctor of Civil Law on 10 March 1566. 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, 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. In 1569 the Queen granted him the
prebend of
Compton Dundon,
Somerset. Wolley first became a
Member of Parliament in 1571, when he was elected for
East Looe. He continued to serve as member for various constituencies for the remainder of his life, being elected for
Weymouth and Melcombe Regis in 1572, for
Winchester in 1584 and 1586, for
Dorset in 1589 and for
Surrey in 1596. stating that he was doing so 'at the desire of my singular good patron, the
Earl of Leicester'. Although Carlyle and Parry state that Wolley had purchased an estate at
Pyrford,
Surrey, by 1576, and that the Queen honoured him with a visit there in that year, other sources state that Pyrford was owned by
Edward Clinton, 1st Earl of Lincoln, until his death in 1585, and that it was Lincoln whom the Queen visited at Pyrford from 12–15 May 1576. It was not until 1589 that Henry Weston obtained licence to alienate Pyrford to Wolley. On 11 October 1577 the Queen created Wolley
Dean of Carlisle, although he was not an ecclesiastic. Wolley was appointed to the
Privy Council on 30 September of that year, and on 25 October was one of the commissioners who tried and convicted the Scottish Queen. who had had custody of the warrant for Mary's execution, and Wolley was one of the commissioners appointed to examine Davison for 'expediting' Mary's death. Wolley was knighted in 1592, 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. 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. Wolley's copy of the latter contains his signature, and after Wolley's death was in the library of the poet,
John Donne. Wolley made his will on 26 February 1596, and died two days later at his house at Pyrford. He was buried in
Old St Paul's Cathedral. 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. ==Marriages and issue==