Battle of Winchelsea - Wikipedia

On August 29, 1350, the Battle of Winchelsea (or Les Espagnols sur Mer): The English naval fleet under King Edward III defeats a Castilian fleet of 40 ships. From the article:

"By the afternoon of 29 August the English fleet was off Dungeness. At 4.00 pm they sighted de la Cerda's force moving towards them with an easterly wind behind. The king was sitting on the deck of his ship, with his knights and nobles, listening to his minstrels playing German airs, and to the singing of young John Chandos.[b] 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. There being no effective naval artillery at the time, battles at sea consisted of grappling with and boarding enemy vessels. In order that the Castilians not sweep past them on the wind, the English also ran before the wind, but with shortened sails so as to allow themselves to be overtaken. There seems to have been an hour before fighting commenced.[6] The difficulty of the manoeuvre is attested to by the King's own ship, the Cog Thomas, striking the Castilian it was attempting to grapple so heavily as to spring its timbers. At the second attempt it successfully grappled and archers deterred Castilians attempting to drop large rocks from their higher deck. Using scaling ladders the men at arms boarded and cleared the deck. Edward transferred his flag, as Cog Thomas was clearly sinking. His son, Edward Prince of Wales, had a similar experience, his men reportedly barely fighting their way aboard their opponent before their own ship foundered, aided by Henry of Lancaster attacking from the other side.

This encouraged the prince's party, and presently the Spaniard surrendered. Her entire crew was, nevertheless, as was the custom in that age, and long afterwards, flung overboard. The prince and his followers had barely time to crowd into the prize before their own craft foundered.[6]

La Cerda's crossbowmen did much execution, firing from their elevated positions. The higher-built and heavier Castilian vessels were able to drop bars of iron or other weights on the lighter English vessels, causing serious damage. The conflict was continued until twilight. At the close the English vessel La Salle du Roi, carrying the king's household, and commanded by the Fleming, Robert of Namur,[c] was grappled by a larger Castilian, and was being dragged off by him. A Flemish valet of Robert of Namur, named Hannequin, boarded the enemy and cut the halliards of her mainsail with his sword, allowing the Castilian ship to be taken.[7]

King Edward is said to have captured between 14 and 26 of the enemy and it is possible that others were sunk.[d] What his own loss was is not stated, but as his own vessel and the vessel carrying the Black Prince were sunk, and from the peril of La Salle du Roi, it seems likely that the English fleet suffered heavily.[8] Much of this action was visible from the English shore, and the clifftops near Winchelsea were lined with spectators which gave the battle its name.[9]"