Around 1350 Simon Burley (age 10) was raised with Edward "Black Prince" (age 19).

In 1369 Simon Burley (age 29) was captured by the French.

In 1377 Simon Burley (age 37) was confirmed an annual grant of £100 by King Richard II of England (age 9).

Calendars. 12 Feb 1385. Commission to W. Bishop of  Winchester (age 65), Thomas, Bishop of  Exeter, Richard, Earl of Arundel (age 39), Robert, Earl of Oxford (age 23), Thomas, Earl of Nottingham (age 16), Hugh de Segrave (age 89), treasurer of England, Simon de Burley (age 45), under-chamberlain, Nicholas Brembre, mayor of London, John Clanvowe and Robert Plesyngton, knights, Master Walter Skirlawe, keeper of the privy seal, John Waltham, keeper of the rolls of Chancery, John Appelby, dean of St. Paul's, London, Richard Rounhale and Thomas Bacton, clerks,

Calendars. 03 Jan 1388. Appointment, during pleasure, of John Devereux (age 51), knight, to be constable of Dover castle and warden of the Cinque Ports, receiving therefor for the maintenance of himself and the chaplains, servants, watch- men and one carpenter abiding therein, £300. a year, viz. from, wards belonging to the castle £146., from the issues of the customs in the port of Sandwich 100 marks and the residue at the Exchequer, without rendering account, as Simon de Bureley (age 48), knight, late constable and warden, saving to the king chattels of felons and fugitives, fines, ransoms, amercements, etc. from the said ports belonging to the king, for which he is to render account at the Exchequer; provided that he stay in person upon the custody as is reasonably needful and as necessity demands. By K. & C. Mandate in pursuance to the said Simon to deliver the castle to him. Mandate de intendendo in pursuance to the barons, bailiffs, good men and whole commonalty of the liberty of the Cinque Ports.

Calendars. 12 Mar 1388. Grant, for life, to John Devereux (age 51), one of the king's bannerets, of the offices of constable of Dover castle and warden of the Cinque Ports, as held by Simon de Burleye (age 48). By p.s. Vacated because otherwise below.

Froissart. 1397. News of this event was sooner known in France and Flanders than in England. The French rejoiced much at it; for it was commonly reported that there would never be any solid peace between France and England as long as the duke of Gloucester (age 41) lived; and it was well remembered, that in the negotiations for peace he was more obstinate in his opinions than either of his brothers; and, for this reason, his death was no loss to France. In like manner, many knights and squires of the king of England's household, who were afraid of him, for his severe and rough manners, were pleased at his death. They recounted how he had driven the duke of Ireland to banishment, and had ignominiously beheaded that prudent and gallant knight sir Simon Burley, who had been so much beloved by the prince of Wales, and had done essential services to his country. The deaths of sir Robert Trevilian, sir Nicholas Bramber, sir John Standwich, and others, were not forgotten, so that the duke of Gloucester (age 41) was but little lamented in England, except by those who were of his party and manner of thinking.

Froissart. Before 16 Sep 1398. King Richard of England (age 31) was of a temper that, when he took a liking to any one, he instantly raised him to high honours, and had such confidence in him that no-one dared to say anything to his prejudice. At the same time, there had not been a king of England in the memory of man who so easily believed all that was told him. His favourites, however paid no attention to the miserable fate of many of their predecessors; how the duke of Ireland had been banished, sir Simon Burley, sir Robert Tresilian, sir Nicholas Bramber and others had lost their lives, for counsels they had given the king, and for which the duke of Gloucester had taken great pains in their destruction. The duke was now dead, and the favourites of the moment, who continually counselled the king as they pleased, were not sorry, for they imagined no one would now pretend to oppose them. Some about the king's person could not disguise their pride and presumption, especially the earl marshal (age 30), who was in the highest degree of favour. To flatter and please the king, and to show how true and loyal a servant he was, whenever he heard any reports he told them to the king, expecting from such means to rise still higher in favour; but many, thinking to advance, are repulsed. Thus it happened to the earl marshal (age 30).