Background: We present a 67-year-old male with a two-week history of progressive double vision. Past medical history included oropharyngeal SCC, T4N2cM0, post-CCRT, and remote sarcoidosis. Clinically, the patient had multiple cranial nerve palsies affecting bilateral occular motor function. Neuroimaging showed an enhancing mass involving the sella and cavernous sinuses. Whole-body PET showed FDG-avid lesions in the sella and liver. Transsphenoidal biopsy of the sellar mass was obtained for tissue diagnosis. Methods: Details of the case were obtained from the patient’s EMR. Neuroimaging and neuropathology were reviewed with the appropriate subspecialists. A literature search was performed using multiple databases (PubMed, Web-of-Science) and relevant articles were included for review. Results: Sellar mass biopsy confirmed p16+ve SCC, identical to the patient’s known primary malignancy. On review of enhanced skull-base images, there was no evidence of direct tumor extension, favouring hematogenous spread. Conclusions: This case demonstrates the localizing potential of cavernous sinus masses. SCC metastases to the cavernous sinus are rare, and confer a poor prognosis.The presence of a p16 mutation has public health implications, as this mutation demonstrates more frequent and aggressive distant metastatic potential, and as a surrogate marker for high-risk HPV infection, represents a preventable risk-factor for a rapidly increasing cause of head and neck cancer in the Western world.