A 61-year-old woman presented with a very rare case of spontaneous bleeding from an orbital cavernous hemangioma manifesting as sudden onset of ophthalmic pain, proptosis, diplopia, and nausea. Magnetic resonance (MR) imaging and computed tomography (CT) revealed an intraconal, well-demarcated cystic mass with hemorrhage. The mass was immediately removed through a transcranial approach. Histological examination showed that the mass was a cavernous hemangioma. Ophthalmopathy was resolved by surgery. Orbital cavernous hemangioma is very common in adults, but spontaneous bleeding is extremely rare relative to intracranial cavernous hemangiomas. This rare case emphasizes the importance of careful neuroimaging evaluation with MR imaging and CT for diagnosing orbital cavernous hemangioma associated with spontaneous bleeding.