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| | | Henry IV 1366-1413 timeline |
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| 1359 |
| | John of Gaunt marries his cousin, Blanche of Lancaster, heiress to vast estates in the north of England | |
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| 1362 |
| | Edward III gives his son, John of Gaunt, the title duke of Lancaster | |
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| 1367 |
| | Henry, son of John of Gaunt, is born in Bolingbroke castle and so becomes known as Henry of Bolingbroke | |
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| 1377 |
| | 10-year-old Richard II follows his grandfather, Edward III, on the English throne | |
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| 1387 |
| | The Lords Appellant, a group of powerful barons, make political demands on Richard II and defeat the king's forces at Radcot Bridge, near Oxford | |
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| 1387 |
| | Henry is one of the Lords Appellant, who are led by his uncle the Duke of Gloucester | |
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| 1389 |
| | After two years, in which the Lords Appellant have been in the ascendant, John of Gaunt helps Richard II gradually to recover his authority as king | |
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| 1398 |
| | A dangerous feud develops between two of England's most powerful barons, Henry of Bolingbroke (son of John of Gaunt) and Thomas de Mowbray | |
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| 1398 |
| | Richard II banishes Thomas de Mowbray for life and Henry of Bolingbroke for ten years | |
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| 1399 |
| | John of Gaunt dies and Richard II denies Henry of Bolingbroke his Lancastrian inheritance, declaring Gaunt's vast estates forfeit to the crown | |
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| 1399 |
| | Henry of Bolingbroke, denied his inheritance, returns to England to lead an armed rebellion against his cousin the king | |
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| 1399 |
| | Richard II surrenders at Conwy to the forces led by Henry of Bolingbroke | |
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| 1399 |
| | Richard II is deposed by parliament and Boliingbroke is proclaimed king of England, as Henry IV, introducing the royal house of Lancaster | |
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| 1400 |
| | Richard II dies in Pontefract castle, almost certainly starved to death on the orders of the new king - insecure on his throne as an undeniable usurper | |
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| 1400 |
| | The Welsh rise against the English and proclaim Owain Glyn Dwr as their own prince of Wales | |
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| 1402 |
| | The 15-year-old Henry, prince of Wales and the future Henry V, takes personal command of the war against the Welsh | |
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| 1403 |
| | Henry Percy, earl of Northumberland, conspires with Edmund Mortimer against Henry IV | |
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| 1404 |
| | Owain Glyn Dwr captures Aberystwyth and Harlech from the English and sets up an independent Welsh administration | |
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| 1405 |
| | Henry Percy leads a rebellion with Richard le Scrope, Archbishop of York, and flees to Scotland when it fails | |
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| 1405 |
| | Henry IV suffers the first attack of some acute but unidentified illness that recurs frequently in the remaining eight years of his life | |
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| 1406 |
| | On the death of his father, Robert III, James I becomes king of Scotland | |
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| 1406 |
| | James, 12-year-old heir to the Scottish king Robert III, is captured at sea by pirates and handed over to Henry IV | |
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| 1406 |
| | Henry IV has the Scottish prince educated, under guard, at Windsor Castle and demands a large ransom for his release (not paid until 1424) | |
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| 1408 |
| | Driven from Aberystwyth and Harlech, Owain Glyn Dwr loses support - and the last Welsh rebellion fades away | |
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| 1408 |
| | With the end of the threat from Wales, the Prince of Wales becomes more directly involved in government, leading to frequent clashes with his ailing father | |
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| 1408 |
| | Henry Percy invades England from Scotland, and is killed at the battle of Bramham Moor | |
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| 1409 |
| | Henry IV entertains at Eltham Palace the emperor Manuel II Palaeologos, the only Byzantine ruler ever to visit Britain | |
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| 1413 |
| | Henry IV dies in the Jerusalem chamber of Westminster Abbey, partly seeming to fulfil a prophecy that he would die in Jerusalem | |
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| 1413 |
| | Henry V succeeds his father, Henry IV, as king of England | |
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| 1424 |
| | The Scots finally pay the ransom for the release of the Scottish prince, now James I, who travels north to claim his throne | |
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