The authors describe two cases that may represent perineural spread of cutaneous squamous cell carcinoma (SCC) into the orbit. Both cases had cutaneous squamous cell carcinomas in the region of the lateral orbital wall (innervated by the zygomatico-temporal nerve) which were excised. The patients presented some time later with masses in the lateral orbit which were biopsied and shown to be squamous cell carcinoma. At the time of presentation with the orbital masses, no skin or bony lesions were noted either clinically or on CT imaging. The authors suggest SCC presenting in the region of the lateral orbital wall may show perineural spread down the zygomaticotemporal nerve into the orbit with the orbital mass presenting sometime after excision of the skin lesion and without any detectable skin recurrence.