Background: A chronic subdural hematoma (CSDH) is defined as chronic (≥3weeks) intracranial bleeding between the dura mater (which adheres to the skull), and the arachnoid mater which envelops the brain. It is usually traumatic and unilateral but rarely, spontaneous hematoma occurs especially in the elderly. Both could be bilateral. The neurological symptoms are usually non specific and may not be readily recognized in the absence of a clear history of head trauma. This is more so in resource limited environments where there is paucity of diagnostic facilities like the computerized tomography (CT) scan. We present a case of spontaneous bilateral acute on chronic hematoma masquerading as chronic headache in a 56 year old man. Method: The Case file of a 56 year old man admitted to the medical ward of the benue state university teaching hospital with chronic headache as well as literature search on the subject were used. Result: A 56 year old man was admitted with chronic headache and neurological deficits without any history of head trauma. He was found to have bilateral chronic subdural hematoma on CT scanning of the brain with one side showing acute on chronic hemorrhage and was managed conservatively with good outcome. Conclusion: Spontaneous chronic hematoma should be considered early in the diagnosis of chronic headache for improved patient outcomes.