Philip II, father of Alexander the Great, succeeded his brother, Perdiccas III, to the throne of Macedonia in 360 BC. He has been described by historians as a generous king and military genius who managed to achieve his ambitious plans by expanding the Macedonian city-state over the whole Greek territory and the greater part of the Balkan Peninsula. The aim of our study was to present the evidence with regard to the facial injury of King Philip II of Macedonia and discuss the treatment of the wound by his famous physician, Critobulos. We reviewed the literature for historical, archaeological, and paleopathological evidence of King Philip's facial injury. We include a modern reconstruction of Philip's face based on the evidence of his injury by a team of anatomists and archaeologists from the Universities of Bristol and Manchester. In the light of the archaeological findings by Professor Andronikos and the paleopathological evidence by Musgrave, it can be claimed with confidence that King Philip II suffered a significant injury of his zygomaticomaxillary complex and supraorbital rim caused by an arrow as can be confirmed in many historical sources. To the best of our knowledge, this is the first attempt to present the trauma of King Philip II from a maxillofacial surgeon's point of view.