Chronic subdural hematoma (SDH) is a well-known disease entity and is traditionally managed with surgery. However, when associated with spontaneous intracranial hypotension (SIH), the treatment strategy ought to be modified, as classical treatment could lead to unwanted consequences. A 59-year-old man presented with a case of SIH that manifested as a bilateral chronic SDH. He developed fatal extensive pneumocephalus and SDH re-accumulation as a complication of burr-hole drainage. Despite application of an epidural blood patch, the spinal cerebrospinal fluid leak continued, which required open spinal surgery. Chronic SDH management should not be overlooked, especially if the exact cause has not been determined. When chronic SDH assumed to be associated with SIH, the neurosurgeon should determine the exact cause of SIH in order to effectively correct the cause.