Chronic subdural hematoma is a common type of intracranial hemorrhage with higher incidence and unpredictable evolution among elderly people. We present the case of a 73 years old male patient, diagnosed in October 2013 with subacute bilateral subdural hematomas who was admitted in our clinic for worsening of motor function in his left limbs. The cerebral CT performed revealed a right massive chronic subdural hematoma which met the criteria for neurosurgical approach requiring a large craniotomy for complete removal. In this article we review the risk factors associated with an unpredictable evolution and postoperative subdural hematoma recurrence in the elderly.