Non-traumatic acute subdural hematomas are a rare occurrence. Etiologies typically include, but are not limited to, cortical artery bleeding, vascular lesions, coagulopathies and spontaneous intracranial hypotension. A forty-five (45)-year old Korean male with no known comorbidities nor history of head or neck trauma consulted the emergency department due to a ten (10)-day history of dizziness and head heaviness and a two (2)-day history of increasing drowsiness and disorientation. The cranial MRI showed a hyperacute to acute subdural hemorrhage along both cerebral convexities, tentorium, and cerebello-pontine angles. Hence a bilateral posterior parietal craniotomy with evacuation of hematoma was performed. Sensorium initially improved, however, fourteen (14) days post-operatively, the patient’s sensorium again deteriorated, accompanied by new onset anisocoria. The cranial CT showed a recurrence of bilateral subdural hematoma, necessitating a repeat evacuation. No vascular malformations or aneurysms were found through cerebral angiography. Sensorium showed no improvement post-operatively. A follow-up CT scan revealed further compression of the bilateral midbrain and an obliterated perimesencephalic sulcus. At this junction, spontaneous intracranial hypotension was suspected. A Whole Spine MRI was requested, which showed a longitudinal spinal anterior epidural CSF leak from C2 to T1 level. Additional patient history revealed that the patient routinely used a handheld neck massager to relieve neck stiffness. The patient was then managed medically and sensorium gradually improved prior to discharge. This case illustrates the importance of a high index of suspicion and clinical history in the management of bilateral subdural hemorrhages without initial clear etiology.