<b><i>Background:</i></b> Voiding dysfunction (VD) is a potential complication after female midurethral sling operations. <b><i>Objectives:</i></b> Our goal was to assess the rate of obstructive VD after transobturator tension-free tape (TOT) procedures and to find perioperative risk factors (RFs) predicting postoperative voiding problems. <b><i>Methods:</i></b> We have retrospectively evaluated the perioperative data of 397 women who underwent TOT operations. Significant post-void residual (PVR) (>50 mL) was considered as the primary (objective) end point of the study, the voiding difficulty as the secondary (subjective) 1. First univariate analysis and then multivariate logistic regression were performed, with a 5% significance level. <b><i>Results:</i></b> Significant PVR was present in 51 (12.8%) women; catheterization was needed in 21 (5.3%) and reoperation in 3 (0.8%) cases. Seventy women (17.6%) experienced postoperative voiding difficulty. Narrow vagina (<2 cm), older age >70 years, and preoperative voiding difficulty were independent RFs for significant PVR (odds ratio: 5.07, 2.14, 5.38, respectively, <i>p</i> < 0.05). Preoperative overactive bladder syndrome and previous pelvic organ prolapse surgery were considered independent RFs for postoperative voiding difficulty. <b><i>Conclusions:</i></b> Older age, narrow vagina, or preoperative voiding difficulty increases the chance for significant postoperative PVR. These patients should be chosen and counseled appropriately.