Abstract Background: Hemorrhoidal problems are common causes of patient complaints. Most of the hemorrhoid-related issues can be managed conservatively; however, some patients with grade III and IV hemorrhoids are referred for surgical management. Several techniques including classic hemorrhoidectomy and dearterialization with or without Doppler guidance have been described. Although not as frequently performed, the Whitehead procedure remains occasionally utilized. Objectives: The goal of this study is to assess the short- and long-term outcomes of the Whitehead procedure in comparison to the Milligan–Morgan procedure. Design: Retrospective review. Patients and Methods: A review of all patients undergoing surgical treatment for grade III and IV hemorrhoids at 7th city hospital in Kyiv, Ukraine, between 2015 and 2021 was conducted. The rates of perioperative complications of the Whitehead procedures and overall outcomes were compared to the Milligan–Morgan techniques. Main Outcome Measures: Primary outcome included postoperative pain and secondary outcomes included short- and long-term postoperative complications. Sample Size: Three hundred and twenty-three patients were included in the study. Results: One hundred and seventy-three patients underwent the Whitehead procedure and 140 patients underwent the Milligan–Morgan procedure. There was no difference in age, sex, and comorbidities between the groups. There were no statistical differences between short-term complications, but the Whitehead group experienced less pain throughout the 14 days after surgery. All the patients were seen and examined 6 months after surgery; the patients who underwent the Whitehead procedure showed less prolapse when compared to those in the Milligan–Morgan group without increase in other complications. Conclusions: Whitehead hemorrhoidectomy is safe and shows less pain during recovery without remarkable increase in long-term complications. Limitations: This was a retrospective review and non-validated instruments were used in surveys. Conflict of Interest: The authors have no conflict of interest to declare.