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Dislocation of the mandibular condyle into the middle cranial fossa is a rare complication of facial trauma that can have neurological and life-threatening implications. This article discusses the anatomic features that predispose patients to this type of injury, as well as the clinical features and mechanism of injury for this rare type of condylar deformity, to help practitioners recognize this easily overlooked injury and avoid disastrous complications. The article summarizes previously published case reports of this rare complication of condylar trauma and presents a case for which initial diagnosis and a management protocol are described.