A 43-year-old hypertensive male developed a pseudoaneurysm at the site of a superficial temporal artery (STA)-middle cerebral artery (MCA) anastomosis, causing massive intracerebral hemorrhage 5 years after the operation. He first experienced repeated transient ischemic attacks, and cerebral angiography disclosed complete occlusion in the cervical portion of the left internal carotid artery. STA-MCA anastomosis was performed, and the ischemic attacks stopped. Postoperative angiography confirmed patency of the anastomosis and good filling of the cortical branches of the left MCA. Five years after surgery, the patient suffered sudden onset of generalized convulsions and consciousness disturbance. Computed tomography disclosed a massive intracerebral hemorrhage in the left frontoparietal region, and angiography revealed an aneurysmal dilatation at the site of the anastomosis that was not seen before. Emergency evacuation of the hematoma and clipping of the aneurysmal dilatation were performed. The patient recovered well and became ambulatory. Histological examination of the surgical specimen showed collagen tissue, indicating a pseudoaneurysm. Patients who undergo STA-MCA anastomosis, especially hypertensive patients, should be followed up by repeated magnetic resonance angiography to confirm the patency of the anastomosis and cerebral perfusion, and to detect the formation of pseudoaneurysms at the anastomosis site, which can cause fatal bleeding.