February 14th, 1400 - Richard II probably died in Pontefract Castle.

Spring 1400 - Glyndŵr complained to Parliament that Reginald de Grey had seized his land, but his plea was rejected.

September 16th, 1400 - Glyndŵr was proclaimed Prince of Wales in Glyndyfrdwy.

September 18th, 1400 - Glyndŵr and his supporters first attacked Ruthin - the home of his neighbour and enemy, Reginald de Grey.

September 18th-23rd, 1400 - Glyndŵr and his supporters then attacked Denbigh, Rhuddlan, Flint, Hawarden, Holt, Oswestry and Welshpool in quick succession.

September 24th, 1400 - Glyndŵr and his men were defeated at the Battle of Vyrnwy, near Welshpool, by an army led by Hugh Burnell.

September 28th, 1400 - Henry IV left Shrewsbury to invade North Wales on his first ‘Royal Expedition’.

October 15th, 1400 - Henry IV returned to Shrewsbury with little to show for his efforts.

November 8th, 1400 - Henry IV confiscated Glyndŵr's estates and gave them to John Beaufort, his half-brother.