It was hardly to be expected that the events of 1157, which saw the significant reduction in the power of Owain Gwynedd, would bring hostilities between Powys and its north-western neighbour to an end. It is clear that by early 1160 that enmity was breaking out into open conflict once again. A poem by Cynddelw records how Powysian forces – the teulu of Madog and that of his son Llywelyn – had been called to Cynwyd Gadfor in Edeirnion in January to give advice on a crisis that was evidently developing. It would appear that Llywelyn ap Madog was given a section of territory between Rug and Buddugre to patrol. We know from the evidence of the poet Gwalchmai that Madog himself died soon afterwards, around 10 February. The king's presence in Edeirnion in January would be difficult to reconcile with the comment in the Peniarth 20 Brut that he died at Winchester. This element of the 1160 entry in the Peniarth 20 Brut has therefore been received with some scepticism. Thomas Jones noted that the story of the death at Winchester was odd and also made the significant observation that this same chronicle text ‘on more than one occasion had Caer Wynt, “Winchester,” where it is manifestly wrong’.

It seems probable that the record of Madog's death in the Peniarth 20 Brut represents a simple misreading of an abbreviated Latin place name: what the translator read as ‘Winton’ may actually have been ‘Witinton’ (Whittington) or an abbreviation thereof. The chronicle also records that Madog's body was carried back for burial at Meifod. It would of course be a much simpler matter to carry him from Whittington to Meifod than from Winchester. If the last journey that Madog undertook was indeed to Whittington it could have a considerable significance. Whittington was one of a group of castles which also included Overton and Chirk. In the 1160s we find these castles being held for Henry II by Welsh castellans of considerable reputation: the brothers Roger and Jonas de Powis and Madog ap Maredudd's own half-brother Iorwerth Goch. It is possible that Madog had gone to Whittington to meet with one or more of these men, with whom he was certainly on good terms, and in any case it is probable that he met with a royal castellan at Whittington.