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| 1296 | Arrest |  |
| Dec William Douglas is released
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| 1297 | Invasion of England |  |
| Supports William Wallace
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| 1297 | Rule of Essex |  |
| 12th June Essex Edward I declares forfeit all Douglas' lands in Esssex & Northumberland
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| 1297 | Rule of Northumberland |  |
| 12th June Northumberland Edward I declares forfeit all Douglas' lands in Esssex & Northumberland
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| 1297 | Siege of Sanquhar |  |
| Sanquhar Captures Sanquhar castle before being in turn besieged
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| Sanquhar William Wallace defeats the English at Dalswinton & then raises the siege of Sanquhar
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| 1327 | Birth |  |
| Birth of William Douglas, son of Sir Archibald Douglas and Beatrice Lindsay, and nephew of "Sir James the Good", Bruce's trusted deputy
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| 1346 | Battle of Neville's Cross |  |
| 4th Sep Neville's Cross Commands a division of Scots, David II is captured
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| 4th Sep Neville's Cross One of the securities for the payment of David II's ransom following the battle of Neville's Cross, and in consequence of the royal misappropriation of some moneys raised for this purpose
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| 1353 | Assassination |  |
| Ettrick Forest Kills his uncle Sir William Douglas of Liddesdale, a knight, in Ettrick Forest
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| 1356 | Battle of Poitiers |  |
| 18th Sep Poitiers Wounded at Poitiers where Scottish troops supported the French as part of the Auld Alliance
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| 1358 | Birth |  |
| Birth of William Douglas, son of 1st Earl Douglas
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| 1358 | Peerage |  |
| Douglas is created Earl of Douglas, a year after marrying Margaret, sister and heiress of Thomas, Earl of Mar, which brought him the estates of Mar
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| 1363 | Rebellion |  |
| Joins David II in seeking a treaty with England which would have written off Scotland's debt to England in return for depriving his nephew Robert the Steward, formerly an ally of Douglas, of the succession
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| 1371 | Justiciar |  |
| Appointed Justiciar South of the Forth
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| 1371 | Rebellion |  |
| Swears allegiance to Robert II
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| 1373 | Marriage |  |
| Marries Isabel, daughter of Robert II
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| 1384 | Death |  |
| Death of William Douglas
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| 1385 | Invasion of England |  |
| Invades England with the help of Jean de Vienne
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| 1423 | Birth |  |
| Birth of William Douglas, son of 5th Earl Douglas
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| 1425 | Birth |  |
| Birth of William Douglas, son of 7th Earl Douglas
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| 1439 | Death |  |
| Edinburgh Death of William Douglas, executed
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| 1439 | Execution |  |
| Edinburgh Executed by Crichton & Livigstone after a mock trial iin front of the King
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| 1440 | Death |  |
| Executed after a mock trial before James II, the Douglas power is broken
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| 1440 | Execution |  |
| Executed after a mock trial before James II, the Douglas power is broken
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| 1449 | Assassination |  |
| Stirling Castle Assassinated by James II after demanding he give up his clan confederacy
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| 1449 | Death |  |
| Stirling Castle Death of William Douglas, assassinated by James II
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| Stirling Death of William Douglas, assassinated by James II
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| 1660 | Privy Council |  |
| Appointed Privy Councilor, 1st term
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| 1687 | Privy Council |  |
| Appointed Privy Councilor, 2nd term
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| 1689 | Succession |  |
| President of the convention that offers the crown of Scotland to William & Mary
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