Chronic subdural hematoma is a common complication after a head injury, especially in patients with risk factors such as old age, alcoholism, or bleeding tendency. The clinical picture is characterized by headache, dizziness, limb weakness, and altered mental status. Most patients with chronic subdural hematoma can be easily cured by burr hole drainage. We report four rare cases of intracranial hemorrhage following the drainage for chronic subdural hematoma. Two patients received intracerebral hematoma evacuation after the burr hole drainage procedure, and the other two patients received medications and rehabilitation therapy only. After that, these patients were discharged under stable conditions.