Sir Hugh was the eldest of seventeen children, and several of the sons were distinguished men. On the eve of the Battle of Navaretto, Sir Hugh, Sir Philip, and Sir Peter were knighted together by the Black Prince. Their eagerness to fight on land or sea led, on one occasion, to an unfortunate result. In 1378 the Duke of Lancaster was exasperating the fleet under his orders by his 'slow Proceedings and unnecessary delays,' and a part of it set out without him. 'Sir Philip and Sir Peter Courtenay, two brothers who had the Command of some ships, espying some vessels belonging to the enemy, inconsiderately assaulted them, being the whole Spanish Fleet, and though they bravely fought, and defended themselves, yet in the end were beaten, most of them who were good gentlemen of Devonshire and Somersetshire being slain. Sir Peter with some others were taken Prisoners, and Sir Philip was sore wounded but escaped the hands of his enemies.'
Later on Sir Philip was Lord Lieutenant of Ireland, and must have wrestled with enough turbulence and riot to satisfy anyone. His manner of governing seems, at any rate, to have pleased the King, who, whilst Sir Philip was still in office, showered honours upon him--'the Park of Bovey Tracey ... Dartmoor Forest, and the Manour of Bradnich.' He was made 'Steward of all the King's Manours and Stannaries in the county of Cornwall,' and later on was appointed to other posts of importance. Unluckily, Sir Philip's chief principle of action seems to have been that might is right, and complaints being made to the King that he had expelled two of his neighbours from parts of their lands, and imprisoned the Abbot of Newenham, and two of his monks, 'with great force,' the intrepid knight was sent to the Tower. However, after a little while, 'at the request of the Lords and Commons, he was restored to his place and good name.'
William Courtenay, a brother to Sir Philip, was Bishop of London at the critical time when Wyclif's doctrines were first stirring men's minds, and after the murder of Archbishop Sudbury, Bishop Courtenay was translated to Canterbury, and began to take very severe measures against the heretics. A strange event marked a meeting of many dignitaries of Church and State, who had gathered to censure Wyclif's teaching and find means for its extermination. 'When they were just going to begin their business a wonderful and terrible earthquake happened throughout all England, whereupon differs of the suffragans being affrighted thought fit to leave off their business, but the Archbishop encouraged them to go on, and they proceeded to examine Articles of Wickliff, and to give their censure upon them.'