The most frequently occurring malignant tumor of epithelial origin of the head and neck region is squamous cell carcinoma (SCC). It is characterized by loco regional dissemination whilst remote metastasis (RM) is rare. The lung, bone, and liver are the frequent sites for RM whilst involvement of the brain or cavernous sinus has an exceptionally rare occurrence. Owing to its rarity, lack of awareness amongst head neck surgeons, and absence of any evidence-based protocol, the optimal management strategies in this population are controversial and, hence, associated with dismal outcomes. The present case report exhibits a rare presentation of cavernous sinus metastasis in human papillomavirus (HPV)-related primary SCC arising from the lower gingivobuccal complex.