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| 1377 |
| | 10-year-old Richard II follows his grandfather, Edward III, on the English throne | |
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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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| 1400 |
| | The Welsh rise against the English and proclaim Owain Glyn Dwr as their own prince of Wales | |
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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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| 1406 |
| | On the death of his father, Robert III, James I becomes king of Scotland | |
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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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| 1413 |
| | Henry V succeeds his father, Henry IV, as king of England | |
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