
- About 1383: He married Margaret Hamner, daughter of David Hamner. They had a number of children.
- 1386: Glyndŵr appeared as a witness in a notable case heard before a court of chivalry.
- 1400: September – After a quarrel with Reginald De Grey, the Lord of Clwyd, Owain and his supporters attack Ruthin.
- 1400: After this year, he adopted the title 'Prince of Wales', and the Coat of Arms of the Princes of Gwynedd, and the idea of a national parliament and an independent Welsh church.
- 1402: He took Reynold de Grey prisoner. He was later released for a ransom of ten thousand marks, as well as Edmund Mortimer, a young member of the family of the former King, Richard II.
- 1404: Owain captured Harlech and Aberystwyth.
- 1405: 28 February – The Tripartite Indenture between him and two English Lords; Wales and England would be divided between them
- 1405: May – The battle of Pwll Melyn, Owain lost many men at this battle.
- During the next three years, he lost Harlech and Aberystwyth.
- 1410: He was still in possession of his home district and was able to muster sufficient support for a raid on the Shrewsbury border.
- 1412: The last time he was heard from before his disappearance, though some believe he died in Kentchurch or Mornington Straddle, Herefordshire, several years later.
‘More than any leader in our country’s history, Owain Glyndŵr is the one who has best succeeded in uniting and leading Wales against English rule.’ – Aeres Twigg, ‘Owain Glyndŵr’ (Gomer 2007), p. 3