1400: The Duke of Rothesay bigamously marries Mary Douglas. The father of his spurned first wife gains support from Henry IV of England and an English army easily takes Edinburgh, except for the castle, before withdrawing.
1401: David Stewart, 1st Duke of Rothesay is captured by his uncle Robert, Duke of Albany and imprisoned in St Andrews Castle. He is subsequently moved to the Duke of Albany's home at Falkland Palace in Fife.
26 March 1402: The murder takes place in Falkland Palace of David Stewart, 1st Duke of Rothesay, the oldest son of King Robert III of Scotland and heir to the throne. He is killed on the orders of his uncle, Robert Stewart, 1st Duke of Albany.
14 September 1402: The Battle of Homildon Hill near Wooler in Northumberland results in a decisive victory for the English over the Scots.
22 March 1406: Twelve year old King James I is captured by pirates off Flamborough Head in Yorkshire while en route to sanctuary in France. They then hand him over to Henry IV of England.
4 April 1406: King Robert III dies in Rothesay Castle after hearing the news of his son James' capture by the English. James therefore succeeds to the throne as James I at the age of 12 and as a prisoner of Henry IV of England.
1407: The Duke of Albany negotiates a renewal of the long standing treaty of mutual support against England with France.
24 July 1411: At the Battle of Harlaw, 20 miles north-west of Aberdeen, the highland army of Donald of Islay, Lord of the Isles meets the lowland army of Alexander, Earl of Mar, son of the Wolf of Badenoch. At stake is the Earldom of Ross and control of northern Scotland. After an inconclusive day of heavy fighting and heavy casualties, Donald retires to Inverness and Alexander to Aberdeen.
1413: The University of St Andrews is founded as a center for learning and the arts.
1420: Robert, Duke of Albany dies and is succeeded as Governor of Scotland by his son, Murdoch.
4 December 1423: The Treaty of London provides for the release of King James I after eighteen years as a prisoner of the English.
April 1425: James I arrests many members of the Albany family, descendents of his uncle, Robert. James Albany evades long enough to attack Dumbarton and destroy the castle, so justifying a charge of treason against the family.
May 1425: The Scottish Parliament meets in Stirling to try the Albany family for treason. Murdoch and three others are executed and the family is virtually extinguished.
1428: James I summons Alexander, Lord of the Isles and other highland clan chiefs to a meeting in Inverness, and has them arrested. Three are executed as an example, but others including Alexander are later released.
8 February 1429: 1,000 Scots under the command of brothers John and William Stuart try to relieve the French garrison at Orleans in France. The Scots are defeated by the English at Rouvray Saint Denis and both brothers are killed.
August 1436: James I loses considerably credibility after his efforts to besiege the English in Roxburgh Castle fail miserably.
21 February 1437: King James I is assassinated while staying at the Blackfriars monastery in Perth. Queen Joan is injured but escapes with their son James, now James II. She ensures that the conspirators, including relatives of James I, are identified and executed.
8 June 1440: James Kennedy is formally appointed Bishop of St Andrews by Pope Eugenius IV.
24 November 1440: The Livingston and Crichton families seek to secure their joint influence over the young James II by killing the Earl of Douglas and his brother in the presence of the King at Edinburgh Castle.
24 January 1446: The "Battle of Arbroath" takes place over who will succeed to the post of "Bailie of the Regality" at Arbroath Abbey. As many as 600 people are said to have been killed.