The increased operative time and costs represent the main limitations of robotic technology application to bariatric surgery. Robotic platforms may help the surgeon to overcome the technical difficulties in super-obese (SO, BMI ≥ 50 kg/m2) patients, in which multi-quadrant operations could be challenging. We aimed to evaluate the effect of robot-assisted (R) versus laparoscopic (L) approaches in Single Anastomosis Duodeno-Ileal Bypass with Sleeve Gastrectomy (SADI-S) and Roux-en-Y Gastric Bypass (RYGB) in SO and Super-Super Obese (SSO, BMI ≥ 60 kg/m2) patients in terms of outcomes and cost-effectiveness. Bariatric procedures performed from 2012 to 2023 were retrospectively reviewed. The inclusion criteria were BMI ≥ 50 kg/m2, primary SADI-S or RYGB. Operative time (OT), early complications, post-operative stay (POS), overall costs and follow-up data were analyzed. A subgroup analysis for surgical procedures and SSO patients was also performed. Among 4596 patients, 174 RYGB and 91 SADI-S in BMI ≥ 50 kg/m2 patients were selected. After Propensity Score Matching analysis, two groups of patients were identified (laparoscopic and robot-assisted), each one composed of 18 RYGB and 26 SADI-S. Intraoperative and post-operative complication rates and POS were comparable. Mean OT was longer in robotic procedures compared with laparoscopy (199.1 ± 65.7 and 109.5 ± 39.1 min, respectively, p < 0.001). The difference in OT was eliminated after only SSO patients were included in the analysis (172.7 ± 24.1 vs 152.6 ± 26.2 min for R-SADI-S and L-SADI-S, respectively, p = 0.107). Robotic surgeries were associated with higher costs (8134.6 ± 1886.7 and 2386.7 ± 388.2 € in R-RYGB and L-RYGB, respectively; 7996.6 ± 873.1 and 3954.6 ± 631.1 € in R-SADI-S and L-SADI-S). Despite increased costs, robotic approach may represent an added value in more complex cases such as SSO patients.