Background/Objectives: The aim of the study was to compare the perioperative and oncologic outcomes of patients who underwent surgery for colorectal cancer (CRC) performed using laparoscopy or using the Medtronic Hugo™ Robotic-Assisted Surgery (RAS) system. Methods: This is a retrospective comparative single-center study of consecutive minimally invasive surgeries for CRC performed by two colorectal surgeons with extensive laparoscopic experience at the beginning of their robotic expertise. Patients were not selected for the surgical approach, but waiting lists and operating room availability determined whether the patients were in the robotic group or the laparoscopic group. The primary outcome was to compare 30-day postoperative complications according to the Clavien–Dindo classification and the Complication Comprehensive Index (CCI). The secondary outcomes included operating times, conversion rates, intraoperative complications, length of hospital stays (LOS), readmission rates, and short-term oncologic outcomes, such as the R0 resection, the number of lymph nodes harvested, the total mesorectal excision (TME) quality, and the circumferential resection margin (CRM). Results: Of the 109 patients, 52 underwent robotic and 57 laparoscopic CRC surgery. Patient demographic and clinical characteristics were similar in the two groups. There was no significant difference between the robotic and the laparoscopic groups regarding postoperative complications, the Clavien–Dindo classification, and the CCI. They also had similar operating times, conversion rates, intraoperative complications, LOSs, readmission rates, and short-term oncologic outcomes (the lymph nodes harvested, the R0 resection, TME quality, and CRM status). Conclusions: This study reports the largest cohort of CRC surgery performed using the Medtronic Hugo™ RAS system and is the first comparative study with laparoscopy. The perioperative and oncologic outcomes were similar, demonstrating that the Medtronic Hugo™ RAS system is safe and feasible for CRC as compared to laparoscopic surgery, even at the beginning of the robotic experience.