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| 1390 |
| | | On the death of his father, Robert II, Robert III becomes king of Scotland | |
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| c. 1390 |
| | | Fan vaulting becomes part of the Gothic tradition, seen to perfection in the cloisters of Gloucester cathedral | |
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| c. 1397 |
| | | The English king, Richard II, commissions a diptych (the Wilton Diptych) showing himself being presented to the Virgin and Child | |
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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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