1326 - 1394
Fighter and Mercenary in the 100 Years War.

A silver shield with a thick red bar between 3 black calves

Sir Hugh took part in the “Fight of the Thirty” In 1351 Sir Robert Bamborough held the town and castle of Ploermel which was besieged by a large array of men at arms led by Robert de Beaumanoir. Robert finding that the English commander did not sally forth suggested they have a joust with 2 or 3.Sir Robert suggested that each side should select 20 or 30 men and have a proper fight on the open plain near a tree called the mid-way oak (de mi-voie.)
30 a side was agreed.

This account is found in Cheshire Gleanings by Robert Axon 1884 based on an account in the mediaeval chronicles of Jean Foissart and mentions Sir Robert Knollys another Cheshire man who could have been brother or cousin of Sir Hugh.

“The sixty having dismounted, were drawn up in front of each other and at a given signal the combat began and the combatants fought until they were quite exhausted. When a rest was called 4 Frenchmen and 2 Englishmen were dead. Their fight was renewed and the issue if it continued would have been a great victory for the English but for conduct which, though crowned by success, appears to have been somewhat unfair. The Knights were fighting on foot and the English kept a steady unbroken phalanx when one of the French knights remounted his horse and first drawing some distance away rushed the steed with great force and impetuosity against them. Their ranks were thus broken and those overthrown were trampled underfoot. Sir Robert and eight others were killed.”

The Battle of Thirty

OR IN OTHER WORDS
They decided to hold the first international sporting match in history with 30 on each side and the rules of chivalry prevalent.
The first half was hard-fought but when the whistle blew the English were leading 4-2.
After the half time orange the match was restarted and the English were obviously superior until one French knight, with the deviousness of his kind, brought into the field of play a large war horse. He then mounted the destrier, totally against the rules, and proceeded to trample on the English killing 8.
As the match was at a French stadium, without a neutral referee, the French took the day.

Head and shoulders of Sir Hugh

Hugh was born round 1325, in Calveley the son of Richard de Calveley. Aged around 16, Hugh fighting was in France under the command of Sir Thomas Dagworth and following which he fought in Brittany for 23 years. He took part in many battles (it was possible he was at Crecy) and Chevauchées (soldiers on a Chevauchée aimed to create as much destruction, carnage and chaos burning crops and buildings, killing the population and stealing anything valuable before enemy forces could challenge them).
He was knighted for his record and in 1353 returned to England for a year during which time he was pardoned by Edward 3rd for “all felonies, trespasses and outlawries” committed before 10th September 1353. He returned to France in 1354 with a “letter of protection”

In Cheshire Chivalry - Bostock 1980- Hugh is described as

"a hero of the age of chivalry and legend in his own time."

After his pardon Hugh continued to harass the French in Brittany and Normandy and was so successful that soldiers of fortune were drawn to his side. He took many prisoners worthy of ransom and much booty and became a rich man. Sir Hugh was an expert in the art of war.

What was he really like this warrior, this mercenary,this looter and raider?

"Hugh was a giant of a man, with projecting cheek bones, a receding hair line, red hair and long teeth. He had a large appetite eating as much as 4 men and drinking as much as ten. He was kind and chivalrous, honoured among men and of great strength. He was a religious man, whenever he seized booty he had it sprinkled to absolve him of his sins in taking it!"

The Chivalry of Cheshire P.30

Later in life, Sir Hugh began to use his great acquired wealth to benefit the church. This was, perhaps in repentance for the outrages of his career, and with Sir Robert Hawkwood and Knollys he founded a college in Rome.
He put a great deal of money into St. Boniface's Church at Bunbury, founding a college there and a chantry. The chantry in Bunbury was founded in 1385 to sing and pray for his soul.

Bunbury Church

He died in 1394 and an alabaster armed effigy was placed in the church that Ormerod says is

"one of the most sumptous altar tombs which his county can boast"