An 80 year-old man presented subacutely with a well-circumscribed superior orbital mass and associated ipsilateral numbness in the frontal nerve distribution. Histopathology after open biopsy revealed well-differentiated invasive squamous cell carcinoma [SCC]. Though no previous history of cancer was elicited from the patient, his dermatologist reported removing three squamous cell carcinomas from the right forehead in the past ten years. Herein, we report a case of perineural orbital spread of distant primary cutaneous SCC.