Chronic subdural hematoma (CSDH) is a common neurosurgical pathology, yet conflicting opinions exist concerning the pathophysiological processes involved. Many consider CSDH a product of an aged acute subdural hematoma (ASDH) secondary to trauma. Serial imaging, however, has demonstrated CSDH formation in patients without any initial ASDH. To understand the relevance of acute hemorrhage in a cohort of patients with CSDH, transformation from an ASDH were categorized as CSDH-acute transformed (CSDH-AT) and those without any acute hemorrhage at the outset as CSDH-de-novo (CSDH-DN). A cohort of 41 eligible patients with CSDH were included, with baseline imaging after trauma (or spontaneous ASDH) available for assessment of acute hemorrhage. Volumetric analysis of all subdural collections and measurements of baseline atrophy were performed. In 37% of cases, there was an ASDH present on baseline imaging (CSDH-AT), whereas 63% had no acute hemorrhage at baseline (CSDH-DN). The CSDH-ATs developed more rapidly (mean 16 days from baseline to diagnosis) and were smaller in volume than the CSDH-DNs, which developed at a mean delay of 57 days. In 54% of the CSDH-DNs, a subdural hygroma was present on baseline imaging, and there was a wide range of baseline cerebral atrophy. This study provides radiological evidence for two distinct pathways in the formation of CSDH, with CSDH-DN occurring more commonly and often involving subdural hygroma. Further work is needed to understand whether the pathological origin has implications for patient outcome.