Odontogenic sinusitis (ODS) is a common cause of orbital, intracranial, and osseous infectious extrasinus complications. Dental infections can spread to the orbital or intracranial spaces though the sinuses via thrombophlebitis or direct extension, or from the dentition or oral cavity via vascular channels in the maxillary alveolar bone. ODS typically presents with unilateral involvement both clinically and radiographically. Any suspicion for extrasinus spread based on history and physical examination should be followed by appropriate imaging, formal dental evaluation, and, when appropriate, ophthalmology and neurosurgery consultations. This multidisciplinary approach ensures appropriate management of both the acute orbital and intracranial complications.