After a failed laparoscopic adjustable gastric band (LAGB), laparoscopic sleeve gastrectomy (LSG) has been proposed as revisional surgery. Those patients that receive a second restrictive procedure fall into a small subgroup of patients with more than one restrictive procedure (MRP). If also the second restrictive procedure fails, the correct surgical strategy is a challenge for the surgeon. Roux-en-Y gastric bypass (RYGB) may be an option but there is no evidence in the literature on whether the procedure is effective in treating failures after MRP. This study aims to evaluate the influence of the previous number of restrictive interventions (MRP vs single LSG) in the results of RYGB as revisional surgery. We have retrospectively analyzed patients who underwent conversion from laparoscopic sleeve gastrectomy (LSG), or from multiple restrictive procedures (MRP), to RYGB for weight regain (WR) or insufficient weight loss (IWL) between 2009 and 2019. The number of patients analyzed was 69 with conversion to RYGB after LSG and 44 after MRP. The reduction of excess weight (%TWL) at 3, 6, 12, 24 RYGB postoperative months was respectively of 11.03%, 16.39%, 21.43%, and 24.22% in the MRP group, and of 10.97%, 16.4%, 21.22%, and 22.71% in the LSG group. No significant difference was found in %TWL terms after RYGB for the MRP group and the LSG group with an overall %TWL, which was 11.00 ± 6.03, 16.40 ± 8.08, 21.30 ± 9.43, and 23.30 ± 9.91 respectively at 3, 6, 12, and 24 months. The linear regression model highlighted a positive relationship between the %EWL post-bypass at 24 months and the time elapsed only between the LSG and RYGB in the MRP group patients (p < 0.001). RYGB has proved to be a reliable technique with good results in terms of weight loss after failed bariatric surgery both in patients who previously underwent MRP and in those who underwent exclusively LSG. RYGB showed better results in patients who experienced WR than in those who had IWL from previous techniques.