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| 1296 | Arrest |  |
| Dec William Douglas is released |
| 1297 | Invasion of England | |
| Supports William Wallace |
| 1297 | Rule of Essex | |
| 12th June Essex Edward I declares forfeit all Douglas ' lands in Esssex & Northumberland |
| 1297 | Rule of Northumberland | |
| 12th June Northumberland Edward I declares forfeit all Douglas ' lands in Esssex & Northumberland |
| 1297 | Siege of Sanquhar | |
| Sanquhar Captures Sanquhar castle before being in turn besieged |
| Sanquhar William Wallace defeats the English at Dalswinton & then raises the siege of Sanquhar |
| 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 |
| 1346 | Battle of Neville's Cross | |
| 4th Sep Neville's Cross Commands a division of Scots, David II is captured |
| 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 |
| 1353 | Assassination | |
| Ettrick Forest Kills his uncle Sir William Douglas of Liddesdale, a knight, in Ettrick Forest |
| 1356 | Battle of Poitiers | |
| 18th Sep Poitiers Wounded at Poitiers where Scottish troops supported the French as part of the Auld Alliance |
| 1358 | Birth | |
| Birth of William Douglas , son of 1st Earl Douglas |
| 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 |
| 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 |
| 1371 | Justiciar | |
| Appointed Justiciar South of the Forth |
| 1371 | Rebellion | |
| Swears allegiance to Robert II |
| 1373 | Marriage | |
| Marries Isabel, daughter of Robert II |
| 1384 | Death | |
| Death of William Douglas |
| 1385 | Invasion of England | |
| Invades England with the help of Jean de Vienne |
| 1423 | Birth | |
| Birth of William Douglas , son of 5th Earl Douglas |
| 1425 | Birth | |
| Birth of William Douglas , son of 7th Earl Douglas |
| 1439 | Death | |
| Edinburgh Death of William Douglas , executed |
| 1439 | Execution of Douglas, 6th | |
| Edinburgh Executed by Crichton & Livigstone after a mock trial iin front of the King |
| 1440 | Death | |
| Executed after a mock trial before James II, the Douglas power is broken |
| 1440 | Execution of Douglas | |
| Executed after a mock trial before James II, the Douglas power is broken |
| 1449 | Assassination | |
| Stirling Castle Assassinated by James II after demanding he give up his clan confederacy |
| 1449 | Death | |
| Stirling Castle Death of William Douglas , assassinated by James II |
| Stirling Death of William Douglas , assassinated by James II |
| 1660 | Privy Council | |
| Appointed Privy Councilor, 1st term |
| 1687 | Privy Council | |
| Appointed Privy Councilor, 2nd term |
| 1689 | Succession | |
| President of the convention that offers the crown of Scotland to William & Mary |
