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Primary squamous cell carcinoma of the head and neck most commonly metastasizes to the lymph nodes, lung, bone, and liver. Many other rare sites of metastatic disease have been reported. To date, metastatic squamous cell carcinoma of the head and neck to the orbital apex has not been described. Presented are two cases, one tonsil and one parotid primary with metastatic disease to the orbital apex. Many tumors have been found to metastasize to the eye and orbit, but head and neck neoplasms are rarely reported. A review of the literature is presented in addition to the detailed case reports with their radiologic findings and clinical course. Surgical resection followed by postoperative radiotherapy appears the treatment of choice at this time.