14 February - Death of the deposed Richard II in Pontefract Castle. His body is displayed in old St Paul's Cathedral, London, on 17 February before initial burial in Kings Langley Church on 6 March.
February - Henry Percy (Hotspur) leads English incursions into Scotland.
25 July - English invasion of Scotland (1400): Henry IV leads his army north from a muster at York.
14 September - Battle of Humbleton Hill: Northern English nobles led by Sir Henry Percy (Hotspur) and using longbows decisively defeat a Scottish raiding army and capture their leader, the Earl of Douglas.
21 July - Battle of Shrewsbury: Henry IV defeats a rebel army led by "Hotspur" Percy who has allied with the Welsh rebel Owain Glyndŵr. Percy is killed in the battle by an arrow in his face.
8 June - Following the collapse of their revolt, Richard Scrope together with Thomas de Mowbray, 4th Earl of Norfolk, and Scrope's nephew, Sir William Plumpton, are tried by a special commission and beheaded at York. Scrope is the first English prelate to suffer judicial execution.
August - Welsh rebels, assisted by the French, unsuccessfully attack Worcester.
1 March - Parliament meets, and continues to sit until December, when it finally achieves its aims of nominating and ensuring the payment of members of the Royal Council.
30 March - The heir to the Scottish throne, Prince James, having been captured by English pirates on 22 March, is detained in England.
February - Henry Percy, 1st Earl of Northumberland, and Lord Bardolf advance with troops from exile in Scotland to Thirsk where they issue a proclamation that they have come to relieve the people from unjust taxation.
19 February - Battle of Bramham Moor: Thomas de Rokeby, Sheriff of Yorkshire, suppresses the Percy rebellion in the north, Percy and Bardolf both being killed.
September - Henry, Prince of Wales, retakes Aberystwyth from Owain Glyndŵr.
Glass painter John Thornton of Coventry completes the largest medieval window in England, at York Minster.
1409
c. January - The Welsh surrender Harlech Castle to the English.
