Hundred Years' War (1415–53)
By 1449, the French had retaken Rouen. In 1450 the Count of Clermont and Arthur de Richemont, Earl of Richmond, of the Montfort family (the future Arthur III, Duke of Brittany) caught an English army attempting to relieve Caen at the Battle of Formigny and defeated it. The English army was attacked from the flank and rear by Richemont's force just as they were on the verge of beating Clermont's army. The French proceeded to capture Caen on July 6 and Bordeaux and Bayonne in 1451. The attempt by Talbot to retake Guyenne, though initially welcomed by the locals, was crushed by Jean Bureau and his cannons at the Battle of Castillon in 1453 where Talbot had led a small Anglo-Gascon force in a frontal attack on an entrenched camp. This is considered the last battle of the Hundred Years' War.
Edward of Angoulême
Although Richard was only ten years old when he began his reign, towards the end of the 1390s, he began what historians consider to be a period of "tyranny". By the time of Edward's death, England was in the midst of fighting during the Hundred Years' War, which had been started by Edward III. Richard made efforts to end the war, but was unsuccessful due to opposition from his magnates and the French refusing to formally acknowledge their territorial losses by transferring land to the English. In 1399, Richard was imprisoned in the Tower of London and abdicated in favour of his cousin, the Earl of Derby. With Richard's death on 14 February 1400, the direct line of the House of Plantagenet was brought to an end.