A 52-year-old man had loss of vision and black discoloration of the lids of the right eye after a retrobulbar injection of 3 mL lidocaine hydrochloride 2% (Xylocaine). Examination of the right eye revealed no light perception with extensive necrosis of the lids. Anterior segment examination revealed conjunctival pallor, corneal edema, and necrosis of the sclera. This is a previously unreported complication of retrobulbar anesthesia comprising ophthalmic artery occlusion with scleral melt, ocular ischemia, and eyelid necrosis.