Background and Objectives: Minimally invasive surgery, especially the single-site approach, has demonstrated several advantages in the gynaecological setting. The aim of this study was to compare the surgical outcomes of single-site hysterectomy for benign conditions between the traditional laparoendoscopic approach and robotic surgery. Materials and Methods: We consecutively enrolled 278 women between 2012 and 2019 in this multicentre trial. The patients underwent robotic single-site hysterectomy (RSSH) or laparoendoscopic single-site hysterectomy (LESSH) procedures with or without salpingo-oophorectomy for benign indications. Surgical parameters and surgical outcomes were analysed. Results: There was a statistical difference between the two surgical techniques for total operative time (p = 0.001), set-up time (p = 0.013), and anaesthesia time (p = 0.001). Significant differences in intraoperative blood loss were observed (p = 0.001), but no differences were shown for blood transfusion or intraoperative or postoperative complications in the two groups. Conclusions: LESSH outperformed RSSH in terms of surgical performance and clinical outcomes, with no differences in adverse events.