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1337 CE - 1453 CE: The Hundred Years' War between England and France.
1366 CE: Henry Bolingbroke, future Henry IV of England, is born at Bolingbroke Castle.
1381 CE: Henry Bolingbroke, future Henry IV of England, marries Mary of Bohun.
1387 CE: Prince Henry, future Henry V of England, is born at Monmouth Castle.
1387 CE: A group of English barons defeat Robert de Vere and his supporters at the Battle of Radcot Bridge near Oxford.
1388 CE: The 'Merciless Parliament' appoints five Lords Appellants to rule England and sidelines Richard II of England.
1397 CE: Richard II of England begins a purge on the Lords Appellant, who were voted by the 'Merciless Parliament' to rule in his stead. They are executed or exiled, including Henry Bolingbroke.
1399 CE - 1413 CE: Reign of Henry IV of England.
1399 CE: Death of John of Gaunt, son of Edward III of England and Duke of Lancaster. His son Henry Bolingbroke inherits the title and the claim to the throne.
1399 CE: Henry Bolingbroke lands in northern England with a small invading army and marches south.
1399 CE: Richard II of England is imprisoned in the Tower of London by Henry Bolingbroke.
1399 CE: Henry Bolingbroke forces Richard II of England to sign a formal document of abdication.
1399 CE: Parliament officially nominates Henry Bolingbroke as Richard II of England’s successor.
1399 CE: Coronation of Henry IV of England in Westminster Abbey.
1400 CE: The Welsh leader Owain Glyn Dwr declares himself the Prince of Wales.
1400 CE: Death of Richard II of England in Pontefract Castle, Yorkshire.
1403 CE: Henry IV of England defeats rebellious barons at the Battle of Shrewsbury. Prince Henry, future Henry V of England also participates.
1404 CE: The Welsh rebel leader Owain Glyn Dwr captures Harlech Castle.
1406 CE: The 'Long Parliament' haggles with Henry IV of England over state finances.
1406 CE: The young Prince James, future James I of Scotland, is captured after a shipwreck and imprisoned in England for 18 years by Henry IV of England.
1408 CE: Henry IV of England wins the Battle of Bramham Moor against the combined Welsh and English rebels.
1409 CE: A royal army led by the Prince of Wales, future King Henry V of England, recaptures Harlech Castle in Wales.
1413 CE: Henry IV of England dies of illness.
1413 CE: Coronation of Henry V of England in Westminster Abbey.