A 67-year-old male, presented with the complaints of itchy, painless, rapidly enlarging black colored mass arising from his left upper eyelid. Ocular examination revealed a dark colored nodule with overlying crust on the temporal aspect of the left upper eyelid. An excisional biopsy revealed a well-circumscribed tumor composed of anastomosing vascular channels of varying sizes. Lining endothelial cells revealed focal areas of hypercellularity, mild to moderate pleiomorphism. Immunohistochemistry revealed that tumor cells are diffusely immunopositive for CD34. A diagnosis of primary cutaneous angiosarcoma of eyelid was made. Systemic oncological workup for metastatic disease was negative. The patient thereafter underwent wide surgical excision with frozen section control of margins followed by free flap skin graft under general anesthesia to achieve complete surgical resection of the tumor. Thus, although extremely rare, angiosarcoma of eyelid should be considered in the differential diagnosis of unusual or atypical eyelid lesions; the early diagnosis and treatment of which improves the survival rate.