Dislocation of the mandibular condyle into the middle cranial fossa is a rare traumatic injury caused by transmission of upward force through the condyle onto the glenoid fossa resulting in fracture of the fossa and superior displacement of the condylar head. This type of injury occurs when the “safety mechanisms” of the mandible fail or are absent. The authors present the case of a 72-year-old female patient with multiple comorbidities who suffered a subcondylar fracture of the left mandible and dislocation of the right mandibular condyle into the middle cranial fossa after a fall. Bilateral external fixation of the mandible to the zygomatic arch was utilized to minimize operative time and provide definitive treatment. Many factors must be taken into account when determining the treatment modality for this type of injury, and the final decision should be tailored to each individual case based on several factors including the length of time between injury and presentation, concomitant neurologic deficit, age, and stability of the patient. The goals of treatment are reduction of the dislocation, avoidance of neurologic injury, and restoration of mandibular function. A multidisciplinary effort is necessary to optimize patient care.