Cynddylan, or Cynddylan ap Cyndrwyn (Cynddylan son of Cyndrwyn) was a seventh century ruler associated with Pengwern. He is described in the poem Marwnad Cynddylan (Elegy of Cynddylan) as a king of Dogfeiling, a sub-kingdom of Gwynedd near Rhuthun to the north of Powys, in modern-day Wales.
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With the collapse of the Roman Empire and the invasion of the Saxons, the remains of the civitas of the Cornovii held on to their lands in the lowland border regions of Wales (Herefordshire and Shropshire). By the beginning of the seventh century King Cystennin was the dominant ruler in the Old North, while King Cyndrwyn "the Stubborn" ruled Powys. Several Early Welsh saga poems, known collectively but rather misleadingly as Canu Llywarch Hen ("The Poetry of Llywarch Hen"), survive that describe this Brythonic/early Welsh kingdom, however they were probably not composed until some time after the events alluded to and are to some degree mythologised. Cyndrwyn died before 642 when his sons, chief of whom was Cynddylan, joined Penda of Mercia in the defeat of King Oswald of Northumbria at the Battle of Maserfield (Welsh: Maes Cogwy), which may have taken place just outside Oswestry.
Cynddylan is first mentioned in the poems at the Battle of Maes Cogwy when the army of Penda was apparently hard pressed and "Cynddylan brought them aid". One of the poems says that Cynddylan brought "seven hundred men" to the battle, but this round figure is probably symbolic. In the aftermath of victory Penda and Cynddylan seem to have fallen out and Cynddylan, allied with Morfael of Caer Lwydgoed (Lichfield), defeated an Anglo-Saxon army with bishops under the walls of the town, possibly in 655. According to the poems, Cynddylan and his brothers stood and fought at the ford of the River Tren, which may have been the River Tern or the River Trent.
The poem Marwnad Cynddylan (Elegy for Cynddylan), possibly of ninth century composition, mourns the death of Cynddylan, as well as the cycle of poems known as Canu Heledd (Song of Heledd), Heledd being his sister.
Most scholars date the Canu Heledd poems to the ninth century, but they may well be representative of earlier works in the oral tradition which are now lost.