The assault on Usk Castle in 1405 formed the opening phase of what became known as the Battle of Pwll Melyn, fought on 5 May 1405 as part of the Glyndŵr Rising. Following a defeat at the earlier Battle of Grosmont, Welsh rebel forces sought to regain momentum in the North Gwent area. The assault was led by Gruffudd ab Owain Glyndŵr, Owain's eldest son, whose forces made a daring attack against Usk Castle from the north. The castle, which according to the contemporary chronicler Adam of Usk had been put into some condition for defence prior to the attack, successfully repulsed the Welsh assault. The garrison was led by Richard Grey, 1st Baron Grey of Codnor, Sir John Greyndour, Dafydd Gam, and Sir John Oldcastle of Herefordshire, and it appears that Gruffudd had no inkling of the strength of the numbers he faced inside the castle.
Following the repulse of the assault, the Welsh forces retreated northward towards the forest of Monkswood and Mynydd Pwll Melyn, the Hill of the Yellow Pool. The English garrison pursued them and attacked, routing the Welsh in the field. Casualties on the Welsh side were severe, with some sources recording the loss of 1,500 men. Three hundred prisoners were subsequently beheaded in front of Usk Castle. Gruffudd ab Owain was captured during the pursuit, while Owain's brother Tudur was slain in the field. The Abbot of Llantarnam, John ap Hywel, was also killed as he ministered to the dying and wounded. Adam of Usk recorded that from this time forth the fortunes of Owain waned in those parts, and the battle effectively marked the end of the rebellion's strength in south-east Wales.
Adam of Usk's contemporary account captures the ferocity of the English pursuit following the failed assault: the garrison slew many of the retreating Welsh with fire and the edge of the sword, driving them without ceasing through Monkswood, where Owain's son Gruffudd was ultimately taken prisoner. So close was the family resemblance between Owain's brother Tudur, who fell in the field, and Owain himself that some English soldiers were briefly convinced that the Welsh leader had been slain.
Welsh losses recorded at approximately 1,500 killed; 300 prisoners beheaded before Usk Castle. Notable Welsh dead included Tudur ab Owain and John ap Hywel, Abbot of Llantarnam. Gruffudd ab Owain was captured. English casualties not recorded in sources.
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