Spontaneous intracerbral hemorrhage (SICH) and chronic subdural hematoma (CSDH) represent the most common types of intracranial hematoma. However, SICH during the progression of CSDH is a very rare disease entity due to etiologic differences. The purpose of this report is to alert neurosurgeons to the existence of this condition and to consider possible mechanisms. An 87-year-old man presented with a sudden onset of headache, followed by quadriparesis. Brain computed tomography scan revealed CSDH in the left hemisphere and remote SICH in the right basal ganglia. CSDH was treated with burr hole drainage, however, the deep parenchymal hematoma was treated conservatively. The patient had a progressive recovery with a good outcome. We recently experienced a case of SICH that occurred during the progression of CSDH. To our knowledge, this is the first reported case of SICH occurring during the progression of CSDH.