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| 1381 |
| | A poll tax imposed in England provokes widespread unrest, which flares up in the Peasants' Revolt | |
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| 1381 |
| | Wat Tyler, leader of the Kentish rebels, meets Richard II at Smithfield - before being struck and wounded by the Lord Mayor of London | |
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| 1390 |
| | On the death of his father, Robert II, Robert III becomes king of Scotland | |
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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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| 1399 |
| | Richard II cedes his crown to Bolingbroke, as Henry IV, and a few months later dies in Pontefract castle - probably starved to death | |
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