Battle of Winchelsea

The naval Battle of Les Espagnols sur Mer ("the Spaniards on the Sea"), or the Battle of Winchelsea, took place on 29 August 1350 and was a victory for an English fleet of 50 ships commanded by Edward III, with the Black Prince, over a Castilian fleet of 40 ships commanded by Don Carlos de la Cerda. Between 14 and 26 Castilian ships were captured, and some were sunk, while 2 English vessels were sunk and many suffered heavy losses.

Narrative of the battle
Castilian ships had fought against England as the allies or mercenaries of France, and there had been instances of piratical violence between the trading ships of both nations. A Castilian merchant fleet was loading cargoes in the Flemish ports to be carried to the Basque coast. The ships were armed and had warships with them. They were all under the command of Don Carlos de la Cerda, a soldier of fortune who belonged to a branch of the Castilian royal family. On its way to Flanders the Castilian fleet had captured a number of English trading ships, and had thrown the crews overboard. Piratical violence and massacre of this kind was then common on the sea. On 10 August, when the king was at Rotherhithe, he announced his intention of attacking the Castilians on their way home. The rendezvous of his fleet was at Winchelsea, and thither the king went by land, accompanied by his wife and her ladies, by his sons, the Black Prince and John of Gaunt, as well as by many nobles. The ladies were placed in a convent and the king embarked on his flagship, the Cog Thomas, on 28 August. The English fleet did not put to sea but remained at anchor, waiting for the appearance of the Castilians. Its strength is not known with certainty, but Stow puts it at 50 ships and pinnaces.

Don Carlos de la Cerda might easily have avoided the English if he had kept well out in the Channel. But he relied on the size and strength of his 40 large ships, and in expectation of an encounter had recruited a body of mercenaries - mostly crossbowmen - in the Flemish ports. In the afternoon of 29 August he bore down boldly on King Edward's ships at anchor at Winchelsea. When the Castilians hove in sight, the king was sitting on the deck of his ship, with his knights and nobles, listening to his minstrels who played German airs, and to the singing of Sir John Chandos. When the look-out in the tops reported the enemy in sight, the king and his company drank to one another's health, the trumpet was sounded, and the whole line stood out. All battles at that time, whether on land or sea, were finally settled by stroke of sword. The English steered to board the Castilians. The king's own ship was run into by one of the enemy with such violence that both were damaged, and she began to sink. The Castilian stood on, and the Cog Thomas was laid alongside another, which was carried by boarding. It was high time, for the king and his following had barely reached the deck of the Castilian before the Cog Thomas went to the bottom. Other Castilian ships were taken, but the fight was hot. La Cerda's crossbowmen did much execution, and the higher-built Castilians were able to drop bars of iron or other weights on the lighter English vessels, by which they were damaged. The conflict was continued till twilight. At the close the large English vessel called La Salle du Roi, which carried the king's household, and was commanded by the Fleming, Robert of Namur, afterwards a knight of the Garter, was grappled by a big Castilian, and was being dragged off by him. The crew called loudly for a rescue, but were either not heard or, if heard, could not be helped. The Salle du Roi would have been taken if a Flemish squire of Robert of Namur, named Hannequin, had not performed a great feat of arms. He boarded the Castilian and cut the halyards of her mainsail with his sword. The Castilian ship was taken. King Edward is said to have captured 14 of the enemy. What his own loss was is not stated, but as his own vessel, and also the vessel carrying the Black Prince, were sunk, and from the peril of La Salle du Roi, we may conclude that the English fleet suffered heavily. There was no pursuit, and a truce was made with the Basque towns the next year.

The battle with the Castilians on the sea is a very typical example of a medieval sea-fight, when the ships were of the size of a small coaster or a fishing smack, were crowded with men, and when the personal prowess of a single knight or squire was an important element of strength.

The only real authority for the battle is Froissart, who was at different times in the service of King Edward or of his wife, Philippa of Hainault, and of the counts of Namur. He repeated what was told him by men who had been present, and dwells as usual on the chivalry of his patrons. See his Chroniques, iv. 91.

England (Edward III)
• 2 Losses unknown - at least two sunk.

Castile (de la Cerda)
40 ships - Perhaps 24 captured