Headache following interventional procedures is a diagnostic challenge due to the multitude of possible etiologies involved. Presentation can be simple (PDPH alone) or complex (exacerbation of pre-existing chronic headache along with PDPH) or headache associated with a new onset intracranial process. Subdural hematoma is a rare complication of cranio-spinal trauma. Cranial subdural hematoma may present in an acute, sub-acute, or chronic fashion. Diagnosis of a subdural hematoma in the wake of a PDPH is difficult, requiring a high level of suspicion. Delayed diagnosis of subdural hematoma is usually related to failure to consider it in the differential diagnosis. Thorough history, assessment of the evolution of symptoms, and imaging studies may identify the possible cause and help direct treatment. Change in the character of initial presenting symptoms may be a sign of resolution of the headache or the onset of a secondary process. We report a case of acute intracranial subdural hematoma secondary to unintentional dural puncture during placement of a permanent spinal cord stimulator lead for refractory angina. There is need for careful follow-up of patients with a known post-dural tear. Failure to identify uncommon adverse events in patients with complicated spinal cord stimulator implantation may lead to permanent injury.