Gradenigo syndrome comprises a clinical triad: retro-orbital pain, sixth cranial nerve palsy, and purulent otorrhea. This clinical syndrome often arises secondary to petrous apicitis, which is an infection of the petrous apex that may result from the contiguous spread of infection from the ear or mastoid. This syndrome is very rare, and based on the existing literature, the initial approach for treatment involves long-term administration of IV antibiotics, which may resolve the underlying infection related to petrous apicitis, mastoiditis, and/or otitis media.In this case, the patient, a 69-year-old male, had a progression of several symptoms, including recurrent headaches, diplopia, hearing loss, and dysphagia, despite long-term antibiotic therapy and a prior mastoidectomy. Thus, the neurosurgical team decided to intervene via anterior petrous bone resection via the Kawase approach, which unfortunately did not result in the resolution of the patient's symptoms. The patient continued to have symptoms of Gradenigo syndrome, including sixth cranial nerve palsy and was subsequently referred to outpatient follow-up for further management. In this report, we present the patient's case and a brief review of the literature concerning various treatment modalities for Gradenigo syndrome.