Battle of Winchelsea 1350: The Great Anglo-Spanish Naval Battle of the Hundred Years’ Wars

On August 29th of 1350, the Battle of Winchelsea, known also as the Battle of Les Espagnols Sur Mer, was fought off the southern coast England between the fleets of King Edward III of England (b.1312-1377) and the Castilian (Spanish) prince Don Carlos de la Cerda (b.1327-1354). The Channel was and is still today the gateway to south England and during the Hundred Years’ War (1337-1453) it was the site of the oft forgotten Battle of Winchelsea.

The Battle of Sluys 1340 as depicted in an illumination from Froissart's Chronicles

Battle of Winchelsea in 1450

An aggressive English naval strategy from 1340-1429 during the Hundred Years' Wars often led to the piracy of any and all ships crossing or returning from the Channel into the North Atlantic. A greater English strategy protected both the major channel ports and the western Irish sea ports, the English always wary of any French, Scottish, and/or Spanish vessels looking for easy plunder along the coast just as the Vikings of the North had done in pre-Norman times. The French often did and still could raid southern England with impunity, pillaging and sacking several coastal towns during the lengthy conflict.

No stranger to naval battles himself, in the year 1340 King Edward III won a decisive battle off the coast of Flanders at the Battle of Sluys in one of the first great battles of the Hundred Years’ War. Described by Froissart as a “fierce and terrible” battle at sea, tens of thousands died during the battle under arrow, crossbow and cannon fire, and by drowning. One English ship carrying mostly countesses, ladies, and the wives of knights was sunk by French canon fire. A sharp drop in moral must have followed for the English knights, sailors, and men-at-arms, who from a distance, could have heard the screams of their countrymen but were unable to offer them any assistance. 

19th century English depiction of the Battle of Sluys in 1340

One of the French admirals, Nicolas BĂ©huchet was captured and executed in the battle, his body hung from the sails of the king’s flagship, Thomas as gruesome trophy of war. One French ship was taken and nearly 400 slain or nearly dead Frenchmen were found on board. Sluys was such a great (if gruesome victory) that King Edward later commemorated it on a “noble” gold coin, depicting himself in splendor wearing his crown and brandishing a sword on his ship amidst this most magnificent and bloody victory. The Battle of Sluys was significant also because it basically guaranteed that the French and their Genoese and/or Castilian allies would never attempt a large scale naval operation into British waters for the remainder of the medieval age.

King Edward's royal Battle of Sluys coin

Prelude to Battle

In the immediate prelude to Battle of Winchelsea on August 29th, 1350, the Count of Flanders had allowed a Castilian fleet under the command of Don de la Cerda of the house of Castile to moor his war-cogs and galleys around the harbor at Sluys, in what is today Zeeland in the Netherlands. From this sanctuary the Spaniards harassed English shipping, fishing, and other merchant vessels which traversed the channel linking Guyenne (Gascony) and southern England. Learning of this danger King Edward gathered his own fleet at Sandwich setting sail aboard his old, stern war-cog, Thomas with his ten year old son John of Gaunt (b.1340-1399). The king waited for the Castilian fleet at the head of a fifty ship fleet. Chronicles notes he was dressed sharply in a beaver fur hat and black velvet jacket, singing and dancing with his men merrily on the deck of his flagship.

Sir John Chandos (d.1370) sang along with the king’s minstrels to a new German song which he had brought back to Edwards court after touring Bohemia and the other Germanic kingdoms to the east of what was once Prussia. Sir John fought in France during the Hundred Years’ War, most notably at the Battle of Auray in 1364, the final battle in the War of Breton Succession, 1341-1364, a corresponding dynastic dispute directly related to the Anglo-Franco war. He would die from wounds received in a New Years Eve skirmish with the French at Lussac in the year 1370.

King Edward's flagship, Cog Thomas

The Battle of the Spaniards on the Sea

The Spanish fleet of forty vessels soon did arrive at the “hour of vespers” and a chaotic battle ensued in which the course and result was shockingly similar if not more hotly contested that the Battle of Sluys had been ten years earlier. The Castilians galleys had much taller sides and were better armed. As such they were dangerous mismatches for the smaller and slower English war-cogs. In some instances Edwards ships were rammed and nearly split in half by the hulking and powerful multi-masted Spanish ships. Both sides suffered casualties due to cannon fire and projectiles (arrow and crossbow bolts) exchanges from ship to ship. The Castilian galleys not only had cannons but they were armed with ballistas (giant crossbow-artillery) and stone throwing catapults (trebuchets or mangonels) as well.

Utilizing a strategy which consisted of boarding the Spanish ships by using large hooks and wooden boards to ensnare and then to hurl themselves onto the Castilian galleys, the English were fought frantically that day. Fighting tenaciously to climb the side of the Spanish vessels they used sword and other melee weapons at first. Once aboard a brawl ensued which was often hand-to-hand. King Edward's fleet took the day because his sailors and knights were aggressive. They boarded enemy ships whilst abandoning their own-throwing the remaining Castilian sailors overboard after which they would take the ship. The English captured many Spanish ships during this brief but costly naval engagement. At least fourteen or fifteen Castilian galleys were captured in this manner during the Battle of Winchelsea. Another ten or more Castilian ships were sunk and at least three to five English cogs were destroyed or else otherwise severely damaged during the naval melee.

A painting of a battle at the sea during the Hundred Years War

The king’s ship was rammed and sunk but he and his retainers managed to escape aboard a commandeered Spanish ship just as the cog Thomas took water and sunk. They then in all likelihood slaughtered the enemy ships former occupants. The Black Prince’s ship took water and began to sink as well but Henry of Grosmont the Earl & later Duke of Lancaster sailed nearer to the Prince of Wales cog, saving his life and the lives of his men including Sir John Chandos. As night fell, the Battle of the Spaniards on the Sea ended with the rest of the Spanish ships fleeing frantically toward the Low countries behind Don de la Cerda’s flagship. Even though King Edward’s fleet had lost a few ships including the king and his heirs own cogs' they had, nonetheless, won a major victory over the Castilians and their heavily armed Spanish galleys.

Suggested Further Reading

Sir John Chandos: The Perfect Knight by Stephen Cooper (2011, UK).

The Hundred Years War: The English in France 1337-1453 by Desmond Seward (Penguin Books, 1978).

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