When Sir Hugh Calveley returned in his old age to his home in Cheshire, wishing to atone, perhaps, for his ruthless acts, he founded a college at Bunbury for a master, two chaplains, and two choristers. Their chief duty, no doubt, was to pray for the repose of the soul of their benefactor.

Cheshire knights and Welshmen fought side by side at Poitiers. When the Black Prince returned to England he gave the Dee Mills for life to Sir Howell y Fwyall.

An inscription on the wall of the Parish Church of Macclesfield tells us that Perkin a Legh 'serv'd King Edward the Third and the Black Prince his sonne in all their warres in France, and was at the Battell of Cressie, and hadd Lyme given him for that service'. The descendants of the Leghs still live at Lyme Hall, near Disley, where a life-size portrait of the Black Prince hangs in the entrance hall. Sir Perkin married the daughter of Sir Thomas d'Anyers, who received a handsome reward for rescuing the Royal Standard at Crecy from the French. His body lies beneath the d'Anyers monument in Grappenhall Church.

The same inscription at Macclesfield tells us that Perkin a Legh 'serv'd King Richard the Second, and left him not in his troubles, but was taken with him and beheaded at Chester'.

Cheshire was very loyal to the unfortunate Richard, who styled himself Prince of Cheshire, and showed great favour to the ancient earldom. The victory of Crecy was due to the English archers, and among them none were more famous than those of Cheshire. On their return from the wars, Richard's faithful bowmen became his body-guard, and could always be relied upon whenever he wished to strike a blow at his enemies. 'Sleep in peace, Dickon,' they would say to him, 'we will take care of thee, and if thou hadst married the daughter of Sir Perkin of Legh, thou mightest have defied all the lords in England.'

Cheshire men got a very bad name, for they were cruel and bloodthirsty, given to lawless deeds and inspiring terror wherever they appeared. They were safe in Cheshire, for the county was governed directly by the king, and did not yet send representatives to Parliament. The House of Commons itself was overawed by a force of 2,000 Cheshire archers, commanded by seven Cheshire esquires. When the Commons rose against the misgovernment of the king, the unpunished robberies and evil deeds of the Cheshire men were one of the causes of complaint. The bowmen all wore the badge of the White Hart, Richard's own device. There are at the present day many inns in the villages of Cheshire that bear the sign of the White Hart, a reminiscence of the days of Richard and his Cheshire guards.

The enemies of Richard were determined to depose him, and put in his place Henry of Lancaster, son of John of Gaunt. Richard banished Henry, and deprived him of his estates and possessions. When Henry landed with a small force at Ravenspur in Yorkshire, in the year 1399, he was joined by many of the northern lords, chief among whom was the powerful Earl of Northumberland and his son, Harry 'Hotspur'. Richard surrendered to his cousin at Flint, and was brought to Chester 'on a sorry hack not worth a couple of pounds'. He was confined in the tower over the gateway of the Castle at Chester before being removed to Pontefract, where he probably met a violent death, though it was given out that he died of starvation. Perkin a Legh was executed for his loyalty to Richard, and his head fixed on a pole on the highest tower of Chester Castle.

The Cheshire archers struck one more blow in Richard's defence. Hotspur had been made Justice of Cheshire and North Wales by Henry the Fourth, to keep down the turbulent Cheshire men and the Welsh insurgents. He suddenly changed sides, and joined Earl Mortimer and Owen Glendower of Wales in their revolt against the new king.

Hotspur gave out that Richard was yet alive at Sandiway, and the chief barons of Cheshire, the Venables and the Vernons, and the archers of Macclesfield and Delamere flocked to his standard. The Mayor of Chester went too, and the parsons of Pulford, Davenham, Rostherne and other villages, each with his own following. Though they were afterwards told that Richard was really dead, they were quite content to avenge him, and the army decked with the badge of the White Hart marched from Cheshire to join the Welsh leader.

King Henry met them near Shrewsbury, where a fierce battle took place. The Cheshire archers fought with great bravery, and even routed a portion of the king's army. But they were gradually overcome by the more numerous royal forces, and Henry's victory was complete. Hotspur himself was killed, and among the slain were 'the most part of the knights and squires of the county of Chester'. After the battle, the baron of Kinderton, Sir Richard Venables, was executed, and his estates given to his brother, a supporter of the king.