c 1335-59

Owain ap Gruffydd Fychan (Owain Glyn Dŵr) born.

c 1375

Owain studies law at the Inns of Court in London.

c 1383

Marries Margaret, daughter of Sir David Hanmer.


Military service under Sir Gregory Sais at Berwick on Tweed with his brother Tudur.



Takes part in King Richard II`s attack on Scotland.


Owain and Tudur enter the service of the Earl of Arundel as esquires.


Takes part in King Richard’s expedition to Ireland.


Richard II deposed and murdered. Henry Bolingbroke takes over the throne as Henry IV. Henry proclaims his son, Henry of Monmouth (later to become Henry V), “Prince of Wales”.


Owain complains to Parliament that Lord Grey of Ruthin has seized some of his lands. Owain’s followers proclaim him Prince of Wales at Glyndyfrdwy on September 16th. Owain and his allies attack and burn Ruthin, then move on to Denbigh, Rhuddlan, Flint, Hawarden and Holt, as well as Oswestry and Welshpool. They are defeated in a battle north of Welshpool. Henry IV, on his way back from Scotland, heads for Shrewsbury, then proceeds through North Wales to Anglesey, burning and looting. He confiscates the estates of Owain and his relatives.


April 1st
(Good Friday)

Gwilym and Rhys ap Tudur capture Conwy Castle. Prince Henry and Hotspur (son of the Earl of Northumberland) are put in charge of pacifying Wales.


Battle of Hyddgen, near Plynlimon; Owain`s forces victorious. He proceeds into Radnorshire.


King Henry makes a second march into Wales, plundering, and executing men loyal to Owain. Aberystwyth and Harlech castles are now besieged by Owain`s men but they fail to capture the castles. Owain opens diplomatic negotiations with King Robert of Scotland, thus declaring himself an independent sovereign.



Owain captures Lord Grey of Ruthin


Battle of Pilleth (Bryn Glas). Owain defeats Edmund Mortimer; the king fails to ransom Mortimer, who  then joins Owain.


Owain invades Glamorgan and Gwent.


King Henry again leads a campaign into Wales, but this is rained off!


Edmund Mortimer marries Owain`s daughter Catherine.



Henry, “Prince of Wales”, attacks and burns Owain`s houses at Sycharth and Glyndyfrdwy. Owain invades in southwest Wales via Brecon; Carmarthen and Newcastle Castles are captured.

July 21st

Prince Henry's army defeats and kills Hotspur at Shrewsbury (Hotspur is Mortimer’s brother-in- law.)


The king’s fourth campaign into Wales. Ineffectual.


A French fleet joins Owain in attacking Caernarfon Castle.



Aberystwyth and Harlech castles captured by Glyn Dŵr.


By now Owain is in command of most of Wales but the English still hold Edward I’s great castles on the  fringe of North Wales.


Owain holds a Parliament at Machynlleth (and probably one at Harlech the following year). Crowned Prince of Wales.



Tripartite Agreement between Owain, Edmund Mortimer and the Earl of Northumberland (Hotspur’s father). Under this Owain will rule Wales and the border shires, while Mortimer gets southern England and Northumberland the north. The boundaries of Wales extend to the sources of the Mersey and Trent, and to within a few miles of Birmingham.

March 11

Prince Henry’s forces defeat a Welsh army which is attacking Grosmont Castle.

May 5th

Battle of Pwll Melyn (near Usk). The Welsh are defeated; Owain`s brother Tudur is killed and Owain`s son Gruffydd is  captured and sent to the Tower (where he later dies).


English forces recapture Beaumaris Castle and loot Anglesey.


A French fleet sails into Milford Haven, joins with Owain`s men and attacks the various English garrisons and towns. They march towards Worcester, but meet Henry IV’s army at Woodbury Hill, near Worcester. This is a stalemate, and the Franco-Welsh force return to Wales.


March 8th

A letter from Charles VI of France inspires the Pennal Letter (now in the French archives) which sets out Owain`s ambitions for Wales - an independent Welsh Church, two Universities etc.


The king attempts to lift the Welsh siege of Coity Castle, but is rained off.


Prince Henry fails to recapture Aberystwyth.



Prince Henry recaptures Aberystwyth Castle. He also captures Harlech Castle (Owain's Court) with it most of Owain`s family. Edmund Mortimer dies during the siege and the rest are sent to the Tower.


Owain and his followers are now fighting a guerrilla war. By c. 1413  Owain is in hiding. Prince Henry has succeeded his father and is now King Henry V; he is willing to make terms, offers a pardon, but Owain does not respond.


What little historical evidence exists suggests Owain Glyn Dŵr died in 1415, but the place and precise date are unknown.


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