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Wykeham is said, in an ancient contemporary account, to have been brought to the Royal Court when he was no more than twenty-three or four, which would be about the year 1348. However, the earliest office which there is recorded evidence for his having held, is that of Clerk of all the King's Works in his Manors of Henley (Oxfordshire) and Easthampstead (Berkshire). His patent for which is dated 10th May 1356. On the 30th October in the same year, he was made Surveyor of the King's Works at the castle and in the Park of Windsor (Berkshire). It is said to have been at the suggestion of the captive King David II of Scots that King Edward pulled down and rebuilt a great part of Windsor Castle. He was certainly encouraged by Wykeham who is thought to have been the architect working under Sir John Brocas & Oliver de Bordeaux, the original Surveyors under the first commission. In the second commission, Wykeham had the sole superintendence of all the work. Queenborough Castle, in the Isle of Sheppey (Kent), was also built under his direction.

The King now began to reward Wykeham bountifully. He had probably taken Deacon's Orders at an early age we find him designated "clericus," or clerk, in 1352. It was not, however, till 5th December 1361 that he was admitted to the Order of Acolyte: he was ordained Sub-Deacon, on 12th March 1362, and priest on, 12th June following. Meanwhile his first ecclesiastical preferment, the Rectory of Pulham in Norfolk, had been conferred upon him by the King's presentation on 30th November 1357. On 1st March 1359, he was presented by the King to the prebend of Flixton in the diocese of Lichfield. On 16th April following, he had a grant of £200 a year from the Crown, over and above all his former appointments, till he should get quiet possession of the Church of Pulham, his induction into which living had been opposed by the Court of Rome. On 10th July in the same year, he was appointed Chief Warden and Surveyor of the King's Castles of Windsor (Berskhire), Leeds (Kent), Dover (Kent), and Hadham, and of the manors of Old and New Windsor (Berkshire), Wychemere (Berkshire) and sundry other castles and manors, with the parks belonging to them. Wychemere (later known as Bear Rails) was his chief residence when attending the King in Windsor. On 5th May 1360, he received the King's grant of the Deanery of the Royal Free Chapel or Collegiate Church of St. Martin-le-Grand, London. In October 1360, he attended upon the King at Calais, probably in quality of public notary, when the treaty of Bretigny was solemnly confirmed by the oaths of Edward and King John of France. Numerous additional preferments in the church were heaped upon him in the course of the next three years. In June 1363, moreover, he had been appointed to the office of Warden and Justiciary of the King's Forests on this side of the Trent. On 14th March 1364, he had, by Royal grant, an assignment of twenty shillings a-day out of the exchequer. On 11th May 1364, he was made Lord Keeper of the Privy Seal and, soon after, he is styled Secretary to the King or what we should now call Principal Secretary of State. In May 1365, he was commissioned by the King, with the Chancellor, the Treasurer and the Earl of Arundel, to treat of the ransom of the King of Scots (David II, taken at the Battle of Neville's Cross in 1346) and the prolonging of the truce with the Scots. Not long after this, he is designated, in a paper printed in the "Foedera,' Chief of the Privy Council and Governor of the Great Council, which phrases, however, Lowth supposes do not express titles of office but only the great influence and authority which he had in those assemblies. "There are several other preferments, both ecclesiastical and civil," adds Lowth, " which he is said to have held; but I do not mention them, because the authorities produced for them are such as I cannot entirely depend upon. And, as to his ecclesiastical benefices already mentioned, the practice of exchanging them was then so common, that 'tis hard to determine precisely which of them he held altogether at any one time." There is extant, however, an account given in by himself on occasion of the bull of Pope Urban V against pluralities, of the entire number and value of his church benefices, as the matter stood in the year 1366; and from this statement, in which Wykeham calls himself "Sir William of Wykeham, clerk, Archdeacon of Lincoln and Secretary of Our Lord, the illustrious King of England, and Keeper of his Privy Seal," it appears that the total produce of those which he had held when the account was demanded was £873 6s 8d, and of those of which he remained in possession when it was given in, £842."

Froissart, speaking of the English Court at this period, says, "At this time reigned a priest called William of Wykeham. This William of Wykeham was so much in favour with the King of England, that everything was done by him, and nothing was done without him."

Part 4: Bishop & Chancellor