Purposes: Little research exists on potential learning curve for male sling procedures. We aimed to perform a learning curve analysis of a single surgeon’s experience of sling placement evaluating multiple outcomes and using the cumulative sum failure methodology. Methods: The study included 65 consecutive patients that underwent implantation of a fixed transobturator sling (TiLOOP Male) for post-radical prostatectomy stress incontinence at our institution from January 2013 to December 2018. Dichotomous outcomes evaluated with cumulative sum failure analysis included 12-months continence defined based on Patient Global Impression of Improvement (PGI-I) questionnaire (primary outcome), 24 h pad test and, 24 h pad use, operative time (⩽/>60 min), and complications (yes/no). Univariate and multivariate logistic regression analyses were performed to evaluate the association of the procedures’ chronological sequence number with the outcomes. Results: Cumulative sum failure curves revealed a clear and lengthy learning curve effect for most of subjective and quantitative continence outcomes and for operative time. For the primary outcome (at least much improved at PGI-I), 62 procedures were required to overcome the learning curve. Accordingly, multivariate analyses showed that the sequence number was statistically significant for predicting failures based on PGI-I (adjusted OR 0.95; 95% CI: 0.91–0.99; p = 0.02), objective outcomes, and operative time. Conclusions: An evident and lengthy learning curve was observed in our series of male sling placement to achieve the end level of proficiency, independently from case-mix. Individualized structured training on male sling surgery will benefit patients treated in the initial surgeon’s experience. Surgical experience should be considered when reporting studies on male slings.