Stress urinary incontinence (SUI) is a significant global health issue that particularly affects females, leads to notable societal and economic challenges and significantly affects the quality of life. This study focuses on the comparative analysis of two established surgical interventions, tension-free vaginal tape (TVT) and transobturator tape (TOT), at a single center and applied to 455 women suffering from SUI, with a mean follow-up period of 102 ± 30 months for TVT and 80.4 ± 13 months for TOT. Our findings indicate that, in comparison to TVT, the TOT procedure demonstrates fewer early and late post-operative complications in patient outcomes (1.41% vs. 17.64% and; 5.66% vs. 12.74%, both respectively). However, the TVT procedure shows a modestly favorable outcome in the risk of recurrence of SUI, compared to TOT (0% vs. 3.7%); the TOT procedure has also proven to be more effective in alleviating of urgency symptoms, although not at a statistically significant level (p = 0.072). Univariable and multivariable analysis of factors that predict late complications showed that only obesity can predict a worse outcome [OR]: 1.125 CI 95%: 1.105–1.533, p = 0.037), when adjustments are made for symptoms presented before surgery and procedure type. While both methods are safe and effective, the choice between them should be based on the specific characteristics of each case.