Management of chronic subdural hematoma (cSDH) poses unique challenges and can be fraught with complications. Understanding the spatial relationships of cSDH to adjacent brain tissue and skull topography is critical for successful surgical treatment. The aim of this report is to highlight the feasibility and efficacy of a novel augmented reality (AR) overlay tool for surgical planning with technical description of two surgical cases using AR for surgical management of cSDH. This report describes a fiducial-less AR system for surgical planning of surgical evacuation of cSDH. The AR system was used to superimpose 3D anatomy onto the patients head to provide image guidance during two cases of evacuation. Imaging demonstrated convexity cSDH. A 3D model of the patient's anatomy was created and registered onto the patients' heads using a novel AR system. Surgical evacuation of the cSDH was completed in each case with surgical planning assisted by AR overlay.