Introduction: Transobturator techniques are frequently used for the surgical treatment of female stress urinary incontinence (SUI), due to their high success rates and few intraoperative complications. However, controversial results have been reported in the literature regarding their incidence. The aim of this study is to analyze the real incidence and trend over time of such complications, especially voiding dysfunctions and overactive bladder (OAB) symptoms. Methods: A comprehensive search using PubMed/MEDLINE, Scopus, and Cochrane databases was performed. The search string used was the following: (female stress urinary incontinence) AND (complication) AND ((midurethral sling) OR (transobturator tape) OR (TVT-O) OR (voiding dysfunctions) OR (de novo OAB) OR (recurrent UTI) OR (vaginal erosion)). We included randomized controlled trials, prospective controlled studies, prospective and retrospective observational studies. All selected articles were screened based on titles and abstracts. Relevant data were extracted and tabulated. Results: A total of 39 studies were included in our analysis. Transobturator tape procedures show a high objective cure rate for SUI, from 76.9% to 100%. Postoperative voiding dysfunctions are shown to be quite common, ranging from 0–22% of cases. Despite that, this percentage decreases to 0–1% after 12 months. De novo OAB incidence ranges from 3% to 14% at 12 months, with variability over time due to multiple factors. Tape-related complications usually occur after 12 months, with a variable incidence up to 7%. Urinary tract infections (UTIs) are quite common in the immediate postoperative period but sometimes can be recurrent, requiring long-term prophylactic antibiotic treatment. Conclusions: Voiding dysfunctions are generally transient complications, while de novo OAB may persist over time. An adequate preoperative counseling, along with accurate written informed consent, could enhance patient tolerance of these issues and contribute to long-term patient satisfaction.