Cadwaladr ap Gruffydd (c. 1100 – 1172) was the third son of Gruffudd ap Cynan, King of Gwynedd, and brother of Owain Gwynedd.
Cadwaladr first appears in the historical record in 1136, when following the killing of the lord of Ceredigion, Richard Fitz Gilbert de Clare, he accompanied his brother Owain Gwynedd in an invasion of Ceredigion. They captured five castles in the north of Ceredigion then later in the year launched a second invasion, inflicting a heavy defeat on the Normans at the Battle of Crug Mawr, just outside Cardigan. In 1137 they captured Carmarthen. He later married Richard Fitz Gilbert de Clare's daughter Alice (Adelize) de Clare and had issue with her.
Gruffudd ap Cynan died in 1137 and was succeeded by Owain Gwynedd, his eldest surviving son. Cadwaladr was given lands in northern Ceredigion. Cadwaladr joined with Ranulph, Earl of Chester in the attack on Lincoln in 1141, when King Stephen of England was taken prisoner. This alliance was probably linked to Cadwaladr's marriage to Alice de Clare, daughter of Richard Fitz Gilbert de Clare.
In 1143 Cadwaladr's men killed Anarawd ap Gruffydd of Deheubarth by treachery, apparently on Cadwaladr's orders. Owain Gwynedd responded by sending his son Hywel ab Owain Gwynedd to deprive Cadwaladr of his lands in Ceredigion. Cadwaladr fled to Ireland where he hired a fleet from Óttar the Norse-Gael king of Dublin and landed at Abermenai in 1144 in an attempt to force Owain to return his lands. Cadwaladr apparently abandoned or escaped from his allies and made peace with his brother, who obliged the Dubliners to leave.