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| 1286 | Birth |  |
| Birth of James Douglas , son of the 1st Lord Douglas |
| 1314 | Battle of Bannockburn | |
| 24th June Bannockburn Commands the left wing |
| 1319 | Battle of Mitton | |
| Mitton Defeats an army under the Archbishop of York |
| 1327 | Battle of Weardale | |
| Weardale Nearly captures Edward III |
| 1388 | Ballad of Chevy Chase | |
| 19th Aug Otterburn Several ballads are later composed in its honour including the battle of Otterburn and the Ballad of Chevy Chase |
| 1388 | Battle of Otterburn | |
| Aug Otterburn After leaving Newcastle Douglas moves in a north-westerly direction, making for the valley of the River Rede, intending to take the same route back to Scotland by which he had entered England |
| 5th Aug Melrose Abbey Death of James Douglas , killed at the battle of Otterburn, the body of Douglas is taken back to Scotland and buried with all honour beside that of his father at Melrose Abbey |
| 19th Aug Otterburn James Douglas has his body hidden in a bush from the English & wins the battle |
| 19th Aug Otterburn Several ballads are later composed in its honour including the battle of Otterburn and the Ballad of Chevy Chase |
| 19th Aug Otterburn War between the Scots and English turned into a feud between the Douglas es & Percys |
| 20th Aug Otterburn The Bishop of Durham was on his way from Newcastle with 2000 cavalry and 5000 infantry, they arrive at Ponteland, where they meet groups of men fleeing from battle, which forces the Scots to retire |
| 1388 | Burial | |
| 5th Aug Melrose Abbey Death of James Douglas , killed at the battle of Otterburn, the body of Douglas is taken back to Scotland and buried with all honour beside that of his father at Melrose Abbey |
| 1388 | Death | |
| 5th Aug Otterburn Death of James Douglas , killed at the battle of Otterburn, the body of Douglas is taken back to Scotland and buried with all honour beside that of his father at Melrose Abbey |
| 1388 | Invasion of England | |
| The Scots begin attacks on both the western and eastern marches, taking advantage of growing divisions between the Percies and the Nevilles, the English wardens |
| Aug Otterburn After leaving Newcastle Douglas moves in a north-westerly direction, making for the valley of the River Rede, intending to take the same route back to Scotland by which he had entered England |
| 20th Aug Otterburn The Bishop of Durham was on his way from Newcastle with 2000 cavalry and 5000 infantry, they arrive at Ponteland, where they meet groups of men fleeing from battle, which forces the Scots to retire |
| 1388 | Siege of Durham | |
| Durham Albany sends Earl Douglas to lay waste the Bishopric of Durham, which he achieves |
| 1388 | Siege of Newcastle | |
| Newcastle Commands 2000 archers and 400 men-at-arms to Newcastle and the north-east |
| 1426 | Birth | |
| Birth of James Douglas , son of 8th Earl Douglas |
| 1449 | Siege of Stirling | |
| Stirling Burns Stirling in revenge for the assassination of his brother William by James II |
| 1525 | Birth | |
| Birth of James Douglas , 4th Earl of Morton, second son of Sir George Douglas of Pittendriech |
| 1543 | Marriage | |
| Marries Elizabeth, daughter of James Douglas , 3rd Earl of Morton |
| 1553 | Peerage | |
| James Douglas succeeds to the title and estates of his father-in-law |
| 1561 | Privy Council | |
| Appointed Privy Councillor |
| 1563 | Lord High Chancellor | |
| Appointed Lord High Chancellor, serves Mary Queen of Scots |
| 1566 | Assassination | |
| Mar Edinburgh Heads an armed force which takes possession of Holyrood palace to effect the assassination of Rizzio |
| Mar Edinburgh Sends a message to obtain Queen Mary's signature to the "bond of security" after the assassination of Rizzio |
| 1566 | Exile of Douglas | |
| Mar Mary escapes to Dunbar, and Morton and the other leaders fled to England |
| 1567 | Conference of Carberry Hill | |
| Carberry Hill Present at the conference at Carberry Hill |
| 1567 | Exile of Douglas | |
| Having been pardoned, Morton returns to Scotland and with 600 men appears before Borthwick Castle, where the Queen after her marriage with Bothwell had taken refuge |
| 1568 | Abdication | |
| Lochleven Takes an active part in obtaining the consent of the Queen at Lochleven to an abdication |
| 1568 | Battle of Langside | |
| 13th May Langside Leads an army which defeats Mary Queen of Scots |
| 13th May Langside Mary & her escort rides off, eventually arriving at Dundrennan Abbey in Dumfries shire, some sixty miles to the south & from here she leaves for England, never to see Scotland again |
| 1572 | Reform | |
| Edinburgh Models the Scottish Church on the Church of England at the Kirk General Assembly |
| Edinburgh The King is to be Governor of the Realm & protector of the Church |
| 1581 | Death | |
| London Charged by Esme Stuart of complicity in the death of Lord Darnley |
| 1581 | Execution of Douglas | |
| London Charged by Esme Stuart of complicity in the death of Lord Darnley |
| 1675 | Birth | |
| Birth of James Douglas |
| 1685 | Rebellion | |
| Commands a regiment of horse against the Duke of Monmouth |
| 1706 | Fellow | |
| Appointed Fellow of the Royal Society |
| 1706 | Royal Society | |
| Appointed Fellow of the Royal Society |
| 1742 | Death | |
| 1st April London Birth of James Douglas |
