The Battle of Arnemuiden
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The Hundred Years War (which actually lasted for 116 years, from 1337 to 1453) was waged over the issue of who had the right to rule France, which was at the time the largest kingdom in Western Europe, and five generations of rival kings sought to rule it.
Although the conflict centered on the two claimants--the rulers of England (the Plantagenets) and those of France, the House of Valois--much of western Europe was dragged into it at one time or another. Scotland; Castile and Aragon (in Spain); Genoa (now part of Italy); Bohemia (Czech); and the Avignon Papacy--a rival to the Pope in Rome--took the French side. England was backed by rebellious Frenchmen; Burgundy (now part of France); Portugal; Navarre (in Spain); and the Papal States loyal to Rome.
The Battle of Arnemuiden took place very early in the war, in September of 1338, between the two main parties to the war, the French and the English. It occurred not far from Arnemuiden, a small port on the island of Walcheren in what was then Flanders--at the time formally a part of France--but is now located in the Netherlands.
Not widely known today, it is remembered by historians for two important "firsts."
For one, it was the first naval battle of the war. The French fleet, which had been built up to ferry Crusaders to the Holy Land, merged with the Castilian and Scottish. A squadron of five English single-masted ships were transporting a huge cargo of wool to Antwerp, to be sold so Edward III of England could pay his allies. Unfortunately for the English, the French fleet badly outnumbered them, and at the end of the day the English commander was forced to surrender.
The equipage of one of the ships, the Christopher, accounted for the second "first" of this battle. That ship bore three cannons, so this was the first naval battle in European history to use artillery. The image of one ship firing at another broadside was first witnessed by Europeans on this day.
When the English surrendered, the French took the wool and the ships into their possession, and slaughtered all the English prisoners.