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.
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.
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".
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.
2 June 1398: The date sometimes given for the landing by Henry Sinclair, 1st Earl of Orkney, in what is thought to be Newfoundland.