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 top s 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 halyard s 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 . Ships involved . England ( Edward III ) . Losses unknown - at least two sunk . Castile ( de la Cerda ) . 40 ships - Perhaps 24 captured