11 min

1369 to 1389

Hundred Years' War: Caroline War

by Something Something

The Caroline War was the second phase of the Hundred Years' War between France and England, following the Edwardian War. It was so-named after Charles V of France, who resumed the war nine years after the Treaty of Brétigny (signed 1360). The Kingdom of France dominated this phase of the war.

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1364 Jan 1 -

Britanny, France

In the Treaty of Brétigny, Edward III renounced his claim to the French throne in exchange for the duchy of Aquitaine in full sovereignty. Between the nine years of formal peace between the two kingdoms, the English and French clashed in Brittany and Castile. In the War of the Breton Succession, the English backed the heir male, the House of Montfort (a cadet of the House of Dreux, itself a cadet of the Capetian dynasty) while the French backed the heir general, the House of Blois. With peace in France, the mercenaries and soldiers lately employed in the war became unemployed, and turned to plundering. Charles V also had a score to settle with Pedro the Cruel, King of Castile, who married his sister-in-law, Blanche of Bourbon, and had her poisoned. Charles V ordered Du Guesclin to lead these bands to Castile to depose Pedro the Cruel. The Castilian Civil War ensued. Having been opposed by the French, Pedro appealed to the Black Prince for aid, promising rewards. The Black Prince's intervention in the Castilian Civil War, and the failure of Pedro to reward his services, depleted the prince's treasury. He resolved to recover his losses by raising the taxes in Aquitaine. The Gascons, unaccustomed to such taxes, complained. Charles V summoned the Black Prince to answer the complaints of his vassals but Edward refused. The Caroline phase of the Hundred Years' War began.

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Battle of Cocherel

1364 May 16 -

Houlbec-Cocherel, France

The French crown had been at odds with Navarre (near southern Gascony) since 1354. In 1363 the Navarrese used the captivity of John II of France in London and the political weakness of the Dauphin to try to seize power. As England was supposed to be at peace with France the English military forces used to support Navarre were drawn from the mercenary routier companies, not the king of England's army, thus avoiding a breach of the peace treaty. In the past when the opposing army had advanced then they would be cut to pieces by the archers, however in this battle, du Guesclin managed to break the defensive formation by attacking and then pretending to retreat, which tempted Sir John Jouel and his battalion from their hill in pursuit. Captal de Buch and his company followed. A flank attack by du Guesclin's reserve then won the day.

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War of the Breton Succession ends

1364 Sep 29 -

Auray, France

At the beginning of 1364, after the failure of the negotiations of Évran, Montfort, with the assistance of John Chandos, came to attack Auray, which had been in the hands of Franco-Bretons since 1342. He entered the town of Auray and besieged the castle, which was blockaded by sea by the ships of Nicolas Bouchart coming from Le Croisic. The battle began with a short skirmish between the French arbalesters and the English archers. Each Anglo-Breton corps was attacked head on, one after the other, but the reserves restored the situation. The right wing of the Franco-Breton position was then counterattacked and driven back and since it was not being supported by its own reserves, it was folded up towards the centre. The left wing then folded in turn, the Count of Auxerre was captured, and the troops of Charles of Blois broke and fled. Charles, having been struck down by a lance, was finished off by an English soldier, obeying orders to show no quarter. Du Guesclin, having broken all his weapons, was obliged to surrender to the English commander Chandos. Du Guesclin was taken into custody and ransomed by Charles V for 100,000 francs. This victory put an end to the war of succession. One Year later, in 1365, under the first Treaty of Guérande, the king of France recognized John IV, the son of John of Montfort as duke of Brittany.

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Castilian Civil War

1366 Jan 1 -

Madrid, Spain

The Castilian Civil War was a war of succession over the Crown of Castile that lasted from 1351 to 1369. The conflict started after the death of king Alfonso XI of Castile in March 1350. It became part of the larger conflict then raging between the Kingdom of England and the Kingdom of France: the Hundred Years' War. It was fought primarily in Castile and its coastal waters between the local and allied forces of the reigning king, Peter, and his illegitimate brother Henry of Trastámara over the right to the crown.

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Battle of Nájera

1367 Apr 3 -

Nájera, Spain

Castilian naval power, far superior to that of France or England, encouraged the two polities to take sides in the civil war, to gain control over the Castilian fleet. King Peter of Castile was supported by England, Aquitaine, Majorca, Navarra and the best European mercenaries hired by the Black Prince. His rival, Count Henry, was aided by a majority of the nobility and the Christian military organizations in Castile. While neither the Kingdom of France nor the Crown of Aragon gave him official assistance, he had on his side many Aragonese Soldiers and the French free companies loyal to his lieutenant the Breton knight and French commander Bertrand du Guesclin. Although the battle ended with a resounding defeat for Henry, it had disastrous consequences for King Peter, the Prince of Wales and England.

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Siege of Limoges

1370 Sep 19 -

Limoges, France

The town of Limoges had been under English control but in August 1370 it surrendered to the French, opening its gates to the Duke of Berry. The Siege of Limoges was laid by the English army led by Edward the Black Prince in the second week in September. On 19 September, the town was taken by storm, followed by much destruction and the deaths of numerous civilians. The sack effectively ended the Limoges enamel industry, which had been famous across Europe, for around a century.

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The Battle of Pontvallain, from an illuminated manuscript of Froissart's Chronicles


Battle of Pontvallain

1370 Dec 4 -

Pontvallain, France

The English had plundered and burnt their way across northern France from Calais to Paris. With winter coming, the English commanders fell out and divided their army into four. The battle consisted of two separate engagements: one at Pontvallain where, after a forced march, which continued overnight, Guesclin, the newly appointed constable of France, surprised a major part of the English force, and wiped it out. In a coordinated attack, Guesclin's subordinate, Louis de Sancerre, caught a smaller English force the same day, at the nearby town of Vaas, also wiping it out. The two are sometimes named as separate battles. The French numbered 5,200 men, and the English force was approximately the same size.

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Battle of Chiset

1373 Mar 21 -

Chizé, France

The French had laid siege to the town and the English sent a relief force. The French, led by Bertrand du Guesclin, met the relief force and defeated it. It was the last major battle in the Valois campaign to recover the county of Poitou, which had been ceded to the English by the Treaty of Brétigny in 1360. The French victory put an end to English domination in the area.

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The Black Prince and Edward III dies

1376 Jun 8 -

Palace of Westminister, Lond

From the period of the Good Parliament, Edward knew that he was dying. His dysentery became violent, and he often fainted from weakness, so that his household believed that he had already died. He died in 1376. Around 29 September 1376 King Edward III fell ill with a large abscess. After a brief period of recovery in February 1377, the king died of a stroke at Sheen on 21 June. He was succeeded by his ten-eventYear-old grandson, King Richard II.

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A 14th-century miniature symbolizing the schism


Western Schism

1378 Jan 1 -

Avignon, France

The Western Schism, also called Papal Schism, The Vatican Standoff, Great Occidental Schism and Schism of 1378, was a split within the Catholic Church lasting from 1378 to 1417 in which bishops residing in Rome and Avignon both claimed to be the true pope, joined by a third line of Pisan popes in 1409. The schism was driven by personalities and political allegiances, with the Avignon papacy being closely associated with the French monarchy. These rival claims to the papal throne damaged the prestige of the office.

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Britanny Campaign

1380 Jul 1 -

Nantes, France

Earl of Buckingham commanded an expedition to France to aid England's ally the Duke of Brittany. As Woodstock marched his 5,200 men east of Paris, they were confronted by the army of Philip the Bold, Duke of Burgundy, at Troyes, but the French had learned from the Battle of Crécy in 1346 and the Battle of Poitiers in 1356 not to offer a pitched battle to the English so Buckingham forces continued a chevauchée and laid siege to Nantes and its vital bridge over the Loire towards Aquitaine. By January, though, it had become apparent that the Duke of Brittany was reconciled to the new French king Charles VI, and with the alliance collapsing and dysentery ravaging his men, Woodstock abandoned the siege.

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Death of Bertrand du Guesclin, by Jean Fouquet


Charles V and du Guesclin dies

1380 Sep 16 -

Toulouse, France

The King died on 16 September 1380 and was succeeded by his 11-eventYear-old son, Charles VI. Du Guesclin died of illness at Châteauneuf-de-Randon while on a military expedition in Languedoc.

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Wat Tyler's Rebellion

1381 May 30 -

Tower of London, UK

The Peasants' Revolt, also named Wat Tyler's Rebellion or the Great Rising, was a major uprising across large parts of England in 1381. The revolt had various causes, including the socio-economic and political tensions generated by the Black Death in the 1340s, the high taxes resulting from the conflict with France during the Hundred Years' War, and instability within the local leadership of London.

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Battle of Roosebeke (Jean Froissart, 1405)


Battle of Roosebeke

1382 Nov 26 -

Westrozebeke, Belgium

Philip the Bold had ruled the council of regents from 1380 till 1388, and ruled France during the childhood years of Charles VI, who was Philip's nephew. He deployed the French army in Westrozebeke to suppress a Flemish rebellion led by Philip van Artevelde, who intended to dispose of Louis II of Flanders. Philip II was married to Margaret of Flanders, Louis' daughter. The Battle of Roosebeke took place between a Flemish army under Philip van Artevelde and a French army under Louis II of Flanders who had called upon the help of the French king Charles VI after he had suffered a defeat during the Battle of Beverhoutsveld. The Flemish army was defeated, Philip van Artevelde was slain and his corpse was put on display.

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Despenser's Crusade

1382 Dec 1 -

Ghent, Belgium

Despenser's Crusade (or the Bishop of Norwich's Crusade, sometimes just Norwich Crusade) was a military expedition led by the English bishop Henry le Despenser in 1383 that aimed to assist the city of Ghent in its struggle against the supporters of Antipope Clement VII. It took place during the great Papal schism and the Hundred Years' War between England and France. While France supported Clement, whose court was based in Avignon, the English supported Pope Urban VI in Rome.

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English invasion of Scotland

1385 Jul 1 -


In July 1385 Richard II, king of England, led an English army into Scotland. The invasion was, in part, retaliation for Scottish border raids, but was most provoked by the arrival of a French army into Scotland the previous summer. Richard's 1385 campaign was considered generally a failure.

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Battle of Margate

1387 Mar 24 -

Margate, UK

In October 1386, Richard II’s so-called Wonderful Parliament approved a commission which began gathering men and ships for a descent (amphibious assault) on Flanders. This was aimed at provoking an insurrection that would replace the government of Philip the Bold with a pro-English regime. On 16 March, Richard, Earl of Arundel arrived at Sandwich, where he took command of a fleet of sixty ships. On 24 March 1387 Arundel's fleet sighted part of a French fleet of around 250–360 vessels commanded by Sir Jean de Bucq. As the English attacked, a number of Flemish vessels deserted the fleet and from there a series of battles commenced from Margate into the channel towards the Flemish coast. The first engagement, off Margate itself, was the largest action and forced the allied fleet to flee with the loss of many ships. Margate was the last major naval battle of the Caroline War phase of the Hundred Years' War. It destroyed France's chance of an invasion of England for at least the next decade.

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Epilogue: Truce of Leulinghem

1389 Jun 1 -

Calais, France

The Truce of Leulinghem was a truce agreed to by Richard II's kingdom of England and its allies, and Charles VI's kingdom of France and its allies, on 18 July 1389, ending the second phase of the Hundred Years' War. England was on the edge of financial collapse and suffering from internal political divisions. On the other side, Charles VI was suffering from a mental illness that handicapped the furthering of the war by the French government. Neither side was willing to concede on the primary cause of the war, the legal status of the Duchy of Aquitaine and the King of England's homage to the King of France through his possession of the duchy. However, both sides faced major internal issues that could badly damage their kingdoms if the war continued. The truce was originally negotiated by representatives of the kings to last three years, but the two kings met in person at Leulinghem, near the English fortress of Calais, and agreed to extend the truce to a twenty-seven years' period. Key Findings: - Joint crusade against the Turks - English support of French plan to end the Papal schism - Marriage alliance between England and France - Peace to the Iberian peninsula - English evacuated all their holdings in northern France except Calais.

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  • Nicolle, David (2011). The Great Chevauchée: John of Gaunt's Raid on France 1373. Oxford: Osprey Publishing. ISBN 978-1849082471.
  • Perroy, E., (1951). The Hundred Years' War. New York, New York: Oxford University Press.
  • Rogers, Clifford (2006). "Chevauchée". International Encyclopedia of Military History. London: Routledge. ISBN 978-0415936613.
  • Wagner, John A (2006). Encyclopedia of the Hundred Years War. Westport CT: Greenwood Press. ISBN 0-313-32736-X.

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