Objective: Chronic subdural hematoma (cSDH) is a common neurosurgical condition in elderly patients, frequently associated with trauma, anticoagulant use, and chronic comorbidities. While surgical evacuation and now middle meningeal artery embolization remain the predominant treatment options, endoscopic-assisted techniques have been increasingly used as a surgical adjunct. We evaluated the safety, clinical outcomes, and recent advancements in endoscopic-assisted evacuation of cSDH through both a retrospective case series and an updated review of the current literature. Methods: A retrospective analysis of 39 patients undergoing 44 endoscopic-assisted evacuations of subdural hematomas between October 2021 and May 2025 was performed. Patient demographics, imaging, operative details, complications, and recurrence were analyzed. A systematic review of 16 studies published between 2022 and 2025 was added to a prior review performed by our group to assess outcomes associated with endoscopic approaches to cSDH. Results: Of the 39 patients (67% male, ages 20 to 73), four experienced recurrence, three prior to middle meningeal artery (MMA) embolization and one after. All patients received postoperative subdural drains, and no intraoperative complications related to the endoscope occurred. The literature review included an additional 16 recent studies (n=1060 patients) in addition to 13 studies from a previous systematic review, reporting recurrence rates of 0% to 16.7%. Endoscopic evacuation was associated with reduced recurrence, shorter hospital stays, and improved hematoma clearance compared to traditional techniques. Limitations included variability in surgical technique across studies and lack of randomized data. Conclusion: Endoscopic-assisted evacuation of cSDH appears to be a safe and effective adjunct to conventional surgical methods through improved visualization, potential coagulation of distal meningeal artery territories, and reduced recurrence. While results are promising, larger prospective studies are needed to confirm long-term benefits and refine patient selection.