Introduction: The ADA produced a triple composite outcome that summarises the therapeutic targets of the three most prevalent complications of obesity: type 2 diabetes (T2D), hypertension and dyslipidemia (HbA1c<7.0%; LDL cholesterol<100 mg/dL and systolic blood pressure <130 mmHg). The present study primarily investigates the difference between Vertical Sleeve gastrectomy (VSG) and Roux-en-Y Gastric Bypass (RYGB) in achieving the composite target one year after the surgery. The secondary outcome assessed the success rate in achieving the separate components’ target at months 6, 12 and 24 post-surgery. Methods: This retrospective observational study evaluated 103 patients with obesity and T2D. At each visit, anthropometric measurements were recorded, and the metabolic and lipid profile was assessed before surgery and subsequently during the follow-up visits at 6, 12 and 24 months post-surgery. Results: Twelve months after surgery, patients undergoing RYGB did not show a significant difference compared to those undergoing VSG in achieving the composite target (p=.57). Patients undergoing RYGB showed greater LDL target achievement at 6 months post-surgery than the VSG (p=.005). Total and LDL cholesterol were significantly reduced over time in the RYGB compared to the VSG (p=.023 and p=.010, respectively). Conclusion: RYGB and VSG showed similar efficacy in reaching the cardiometabolic ADA composite target in subjects with T2D undergoing bariatric surgery. Patients undergoing RYGB showed a significant reduction in LDL and total cholesterol over time compared to the VSG group. More extended randomised studies are needed to evaluate the effectiveness of the two surgical procedures in improving and remission cardiovascular risk factors associated with obesity.