Chronic subdural hematoma (cSDH) is one of the most common neurosurgical entities, especially in the elderly population. Diagnosis is usually established via a head computed tomography, while an increasing number of studies are investigating biomarkers to predict the natural history of cSDH, including progression and recurrence. Surgical evacuation remains the mainstay of treatment in the overwhelming majority of cases. Nevertheless, many controversies are associated with the nuances of surgical treatment. We performed a systematic review of the literature between 2010 and 2022, aiming to identify and address the issues in cSDH surgical management where consensus is lacking. The results show ambiguous data in regard to indication, the timing and type of surgery, the duration of drainage, concomitant membranectomy and the need for embolization of the middle meningeal artery. Other aspects of surgical treatment—such as the use of drainage and its location and number of burr holes—seem to have been adequately clarified: the drainage of hematoma is strongly recommended and the outcome is considered as independent of drainage location or the number of burr holes.