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Purpose To describe two unusual cases of osseous metaplasia occurring within the eyelid and to present a brief review of the literature on cutaneous calcification. Methods Case reports and literature review. Results A 62-year old man presented with an eyelid mass containing osseous metaplasia in an area of lymphoid hyperplasia. An extensive oncologic workup ruled out malignancy. A 46-year old man with a history of recurrent chalazion presented with a firm mass of the upper eyelid that demonstrated bone formation in the area of a metaplastic sebaceous gland. Both lesions were excised with no further recurrence. Conclusions Osseous metaplasia of the eyelid is a rare entity with diverse etiologies ranging from congenital syndromes to trauma, neoplasm, and inflammation. In some cases, a precise etiology cannot be identified.