20 January 1356: Edward Balliol relinquishes his claim to the Scottish Crown to King Edward III of England in exchange for an English pension.
3 October 1357: The Treaty of Berwick is signed at Berwick-upon-Tweed, ending the Second War of Scottish Independence and releasing King David II from English captivity.
October 1357: David II is released in return for a ransom of £65,000. He returns to a country heavily under the influence of Robert Stewart, who has been acting as "King's Lieutenant" for eleven years.
22 February 1371: King David II dies at Edinburgh Castle. He is succeeded by his nephew, Robert Stewart who becomes King Robert II, and the founder of the Stewart dynasty that is to rule Scotland for most of the next three hundred years. Robert II is the grandson of Robert the Bruce by his daughter Marjory.
24 October 1378: The birth of David Stewart, 1st Duke of Rothesay. Also known as Prince David, he was the oldest son of King Robert III of Scotland and heir to the throne.
November 1384: An ailing Robert II is sidelined in favour of his own eldest son and heir, John, Earl of Carrick, who becomes Guardian of the Kingdom.
1385: Archibald Douglas, 3rd Earl of Douglas captures Lochmaben Castle from the English, held by them since 1333.
June 1385: The Scots under the Earl of Carrick, supported by a French army, invade northern England but are pushed back as far as Edinburgh, which is destroyed in retaliation by the English.
1387: Donald of Islay becomes the 2nd Lord of the Isles following the death of John of Islay.
August 1388: The Earl of Carrick leads the Scots into Cumberland and Northumberland. This culminates with the Battle of Otterburn, a victory for the Scots but with the loss of their battlefield commander James, Earl of Douglas, the Earl of Carrick's most powerful ally in southern Scotland.
5 August 1388: Scottish troops under James Douglas, 2nd Earl of Douglas, decisively defeat an English army at the Battle of Otterburn in Northumberland.
December 1388: John, Earl of Carrick, who has been injured while riding, is replaced as Guardian of the Kingdom by his younger brother Robert, Earl of Fife.
19 April 1390: The death at Dundonald Castle of King Robert II, the son of Robert I's daughter Marjorie and her husband Walter Stewart, 6th High Steward of Scotland.
17 June 1390: Alexander Stewart, youngest son of Robert II and younger brother of John, Earl of Carrick (now Robert III) and Robert, Earl of Fife destroys Elgin Cathedral in reprisal against Bishop Alexander Bur. He is better remembered as the "Wolf of Badenoch".
24 July 1394: Alexander Stewart, 1st Earl of Buchan, the Wolf of Badenoch dies, according to legend after playing chess with the devil at Ruthven Castle.
28 September 1396: The Battle of the Inch, or the Battle of the Clans, is organised on Perth's North Inch by King Robert III in an effort to end a long standing feud between the Kay and Chattan Clans.
13 March 1395: The death in Aberdeen of John Barbour, the churchman and poet and the first important author to write in the Scots language.
1398: Robert III's eldest son, David, is created 1st Duke of Rothesay and Robert III's younger brother, Robert, Earl of Fife, is created Duke of Albany.
2 June 1398: The date sometimes given for the landing by Henry Sinclair, 1st Earl of Orkney, in what is thought to be Newfoundland.
1399: The General Council takes power from Robert III, now in poor health, and gives it instead to David Stewart, 1st Duke of Rothesay, who they make the King's Lieutenant.
