Introduction: The use of Transit Bipartition with Sleeve Gastrectomy (SG + TB) to treat obesity and type 2 diabetes related to it has been increasing, but there are many challenges related to the procedure. The anastomosis diameter of gastroileostomy (GI) performed using linear staplers is an important factor affecting the postoperative metabolic status. Aim: We aimed to compare linear-stapled (LS) and circular-stapled (CS) GI in SG + TB in terms of early and late perioperative and postoperative status. Material and methods: This retrospective study included 24 patients who had undergone SG + TB between January 2018 and June 2019 to treat obesity and/or type 2 diabetes. GI was performed using linear staplers in 13 (SG + TB-LS group) and circular staplers in 11 patients (SG + TB-CS group). Operative time, hospitalization duration, complications, body mass index, haemoglobin A1c, albumin, haemoglobin, etc. were compared between the 2 groups before and 12 months after the surgery. Results: The operation time was shorter in the SG + TB-CS group than in the SG + TB-LS group. The surgical treatments were successful in both groups in terms of weight loss and diabetes remission. Although not statistically significant, malnutrition and anaemia were slightly higher in the SG+TB-LS group than in the SG + TB-CS group during the follow-up process. Conclusions: Both anastomosis types were found to be safe for SG+TB, and the risks of postoperative complications were low and comparable in both groups. However, the diameter of the anastomosis should always be the gold standard in the CS technique, while it may be too wide or too narrow in the LS technique.