Acute spontaneous subdural hematoma of arterial origin, a neurosurgical emergency resulting from rupture of the perisylvian cortical artery, is a rare occurrence. We report four such patients who presented with progressive neurological deterioration. All the patients were operated and perisylvian cortical artery was identified as the source of bleeding in all the patients. Three of the patients had associated hypertension. We reviewed the clinical characteristics, etiology, and outcome of the reported cases in the literature. A high index of suspicion is necessary even in young patients in view of the phenomenon of re-rupture mimicking stroke. Early diagnosis and a wide craniotomy over the sylvian fissure to obtain hemostasis of bleeding points results in good outcome.