Background: Chronic subdural hematoma (CSDH) is a prevalent type of intracranial hemorrhage. Surgical interventions, such as Twist Drill Craniostomy and Burr Hole Craniostomy, are employed for its treatment. However, limited information exists regarding the impact of postoperative head position (supine vs. elevated) on clinical outcomes. We aim to assess whether patients’ head position after surgery influences their prognosis. Method: We conducted a PRISMA-compliant systematic review and meta-analysis. Our search encompassed PubMed, Cochrane CENTRAL, Scopus, Web of Science, and Embase databases to identify relevant published studies. Data were meticulously extracted, pooled using a fixed model, and reported as risk ratios (RR) with 95% confidence intervals (CI). Statistical analysis was performed using R and Stata MP v.17. Results: Five studies involving 284 patients were included in our meta-analysis. We focused on three primary clinical outcomes, comparing the supine and elevated header positions. Notably, there was no statistically significant difference between the supine and elevated positions in terms of recurrence rate (RR 0.77, 95% CI [0.44, 1.37]), second intervention for recurrence (RR 1.07, 95% CI [0.42, 2.78]) and postoperative complications (RR 1.16, 95% CI [0.70, 1.92]). Conclusion: Current studies have proved no difference between supine and elevated bed header positions regarding recurrence rate, second intervention for recurrence, and postoperative complications. Future RCTs with long-term follow-ups are recommended.