Introduction: Metabolic/bariatric surgery is the only proven treatment for type 2 diabetes mellitus (T2D) with curative intent. However, in a number of patients, the surgery is not effective or they may experience a relapse. Those patients can be offered re-do bariatric surgery (RBS). Purpose: The study aimed to determine factors increasing the odds for T2D remission one year after RBS following primary laparoscopic sleeve gastrectomy. Methods: A multicenter retrospective cohort study was conducted between January 2010 and January 2020, which included 12 bariatric centers in Poland. The study population was divided into groups: Group 1- patients with T2D remission after RBS (n = 28) and Group 2- patients without T2D remission after RBS (n = 49). T2D remission was defined as HBA1c < 6.0% without glucose-lowering pharmacotherapy and glycemia within normal range at time of follow-up that was completed 12 months after RBS. Results: Fifty seven females and 20 males were included in the study. Patients who achieved BMI < 33 kg/m2 after RBS and those with %EBMIL > 60.7% had an increased chance of T2D remission (OR = 3.39, 95%CI = 1.28–8.95, p = 0.014 and OR = 12.48, 95%CI 2.67–58.42, p = 0.001, respectively). Time interval between primary LSG and RBS was significantly shorter in Group 1 than in Group 2 [1 (1–4) vs. 3 (2–4) years, p = 0.023]. Conclusions: Shorter time interval between LSG and RBS may ease remission of T2D in case of lack of remission after primary procedure. Significant excess weight loss seems to be the most crucial factor for T2D remission.