Retrobulbar hemorrhage is a vision-threatening emergency that may occur spontaneously or following facial trauma, orbital surgery, endoscopic sinus surgery, and retrobulbar injections. It may determine visual loss because of central retinal artery occlusion, optic neuropathy from direct compression, or compression of the circulation from mechanical tamponade. In addition to a deterioration in visual acuity with total blindness in the most severe cases, several symptoms and signs can be found, such as a sudden onset of severe pain, proptosis, and ophthalmoplegia.The knowledge of past medical history and underlying medical conditions is crucial in patients with retrobulbar hemorrhages. In fact, patients with blood dyscrasias have to be considered high-risk patients due to their increased propensity for uncontrolled bleeding.The aim of this article was to present and discuss the management of a case of double consecutive retrobulbar hemorrhage in a high-risk patient in treatment with aspirin and warfarin.