The implementation of barbed sutures appears to enhance the process of suturing and knot tying, particularly in the field of bariatric surgery, where they can offer significant advantages. The objective of this study is to evaluate the safety and effectiveness of utilising barbed sutures for gastric pouch-jejunal anastomosis (GPJA) and jejuno-jejunal anastomosis (JJA) anastomosis in Roux-en-Y Gastric Bypass (RYGB). Data from patients who underwent primary RYGB between January 2012 and October 2018 were retrospectively collected using Propensity Score Matching (PSM) to randomise groups (barbed sutures—BS-G and conventional sutures—CS-G). The primary outcome was postoperative early complications. The secondary outcomes were late complications (internal hernias and small bowel obstructions), operative time and postoperative hospital stay. A total of 969 patients were included. After PSM, 322 (161 in BS-G vs. 161 in CS-G) patients were compared (chi-square 0.287, p = 0.862). Postoperative early and late complications were comparable between the two groups. BS-G had a significantly shorter median operative time (65 vs. 95 min p p < 0.001). Barbed sutures effectively reduce the operation duration and are as safe as conventional sutures for closing anastomotic defects during RYGB.