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Background Spontaneous intracranial hypotension (SIH) is a more common than previously noted condition (1–2.5 per 50,000 persons) typically caused by cerebrospinal fluid (CSF) leakage. Initial treatment involves conservative therapies, but the mainstay of treatment for patients who fail conservative management is the epidural blood patch (EBP). Subdural hematoma (SDH) is a common complication occurring with SIH, but its management remains controversial. Methods In this report, we discuss a 62-year-old woman who presented with a 5-week history of orthostatic headaches associated with nausea, emesis, and neck pain. Despite initial imaging being negative, the patient later developed classic imaging evidence characteristic of SIH. Magnetic resonance imaging was unrevealing for the source of the CSF leak. Radionuclide cisternography showed possible CSF leak at the right-sided C7-T1 nerve root exit site. After failing a blind lumbar EBP, subsequent targeted EBP at C7-T1 improved the patient's symptoms. Two days later she developed a new headache with imaging evidence of worsening SDH with midline shift requiring burr hole drainage. This yielded sustained symptomatic relief and resolution of previously abnormal imaging findings at 2-month follow-up. Results A literature review revealed 174 cases of SIH complicated by SDH. This revealed conflicting opinions concerning the management of this condition. Conclusions Although blind lumbar EBP is often successful, targeted EBP has a lower rate of patients requiring a second EBP or other further treatment. On the other hand, targeted EBP has a larger risk profile. Depending on the clinic situation, treatment of the SDH via surgical evacuation may be necessary. [ABSTRACT FROM AUTHOR]