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In 1402 Owain's old enemy, Grey of Ruthin, fell into Glyndŵr's hands, as did the sole adult male of the Mortimer family. In 1404 Owain captured the castles of Aberystwyth and Harlech, sealed an agreement with the French and held a parliament at Machynlleth, where he was perhaps crowned Prince of Wales in the presence of envoys from France, Scotland and Castile.

French assistance arrived in 1405 when virtually the whole of Wales, beyond the environs of royal-held castles, acknowledged the authority of Owain.

Although 1405 represented the climax of Owain's power, the year had its setbacks. The French contribution proved disappointing. Defeats at Grosmont Castle and at Pwllmelyn near Usk undermined Glyndŵr's authority in the south east. By 1406 his main hope was further assistance from France. That March he wrote to the King of France offering to transfer the allegiance of Wales from the Pope in Rome, recognised by England, to the Pope in Avignon, recognised by France.

The letter, written at Pennal near Machynlleth, sought recognition of St David's as an archbishopric with authority over the other bishops of Wales and several of those of England. It called for the appointment of clerics fluent in Welsh, the establishment of two universities in Wales and the retention in the country of the revenues of Welsh churches. The 'usurper', Henry IV, should be excommunicated and the Welsh should have receive full remission for any sins they might commit in the struggle against him.

The French did not respond. Henry IV's son, later Henry V, proved an effective military leader. Aberystwyth Castle was lost in 1408 and Harlech Castle in 1409.

Thereafter, Glyndŵr was a fugitive in the mountains. He probably died in about 1416 at Kentchurch on the Herefordshire border at the home of his daughter Alys. The location of his grave has proved a matter of much speculation.

Glyndŵr's revolt proved devastating for the people of Wales. Chroniclers reported that Glyndŵr 'brought all things to waste' and the English king 'proclaimed havoc in Wales'. It was accompanied by an extensive destruction considered characteristic of peasant revolts - which in some senses it was.

It can also be considered a civil war, for not all Welshmen were prepared to abandon their allegiance to the English crown. At least a generation passed before the economy began recovering. The Welsh gentry, many of whom had supported Glyndŵr, came to the conclusion that their future lay in co-operation with the English authorities.

350 years passed before the significance of the revolt was fully realised. From the late 18th century onwards, Glyndŵr was increasingly recognised as the greatest hero in the history of the Welsh people and his revolt seen as central to the growth of the sense of Welsh nationality.