Background: Being overweight or obese is a risk factor for incontinence and has negative impacts on the surgical outcomes. Compared with trans-obturator sling (TOS), single incision sling (SIS) is a new generation of anti-incontinence surgery. However, the data on SIS in overweight and obese women remains limited. Methods: This retrospective study analyzed the objective and subjective cure rate of overweight and obese women who underwent sling surgeries. Other evaluations included valid questionnaires to assess quality of life and 1-hour pad test to quantify urine leakage. Surgical characteristics and adverse events were also analyzed. Results: A total of 217 patients were analyzed with a median follow-up period of 37.3 months (range, 9–84 months). For overweight and obese patients, the objective and subjective cure rate were comparable (all p > 0.05). However, the SIS group had worse post-operative incontinence-related symptom distress (p < 0.001) and 1-hour pad test (p = 0.047). On the other hand, SIS had a shorter surgery time (p = 0.017) and lower pain score (p < 0.001). Conclusions: Compared with TOS, SIS had non-significant cure rates in the overweight and obese women. SIS had worse urine leakage and incontinence symptoms, but less surgical and wound pain in obese women. Thorough pre-operative counseling is necessary.