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| 1371 |
| | | On the death of his uncle, David II, Robert Stewart becomes king of Scotland as Robert II | |
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| 1390 |
| | | On the death of his father, Robert II, Robert III becomes king of Scotland | |
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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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| 1406 |
| | | On the death of his father, Robert III, James I becomes king of Scotland | |
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| 1408 |
| | | Henry Percy invades England from Scotland, and is killed at the battle of Bramham Moor | |
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| 1437 |
| | | On the death of his father, James I, James II becomes king of Scotland | |
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| 1460 |
| | | On the death of his father, James II, James III becomes king of Scotland | |
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| 1461 |
| | | Henry VI flees to Scotland, abandoning the kingdom to the usurping Edward IV | |
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| 1469 |
| | | The Orkneys and Shetlands come into the possession of James III of Scotland with the dowry of Margaret of Denmark | |
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| 1488 |
| | | On the death of his father, James III, James IV becomes king of Scotland | |
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