Background: Robotic-assisted simple prostatectomy (RASP) proved to be a sound and effective procedure for bladder outlet obstructive symptoms relief. Routinely, the transvesical (Freyer) or transcapsular (Millin) techniques are performed. A novel approach of near-infrared fluorescence imaging (NIFI)-guided urethra-sparing robot-assisted prostatectomy (Madigan) was recently introduced. Objectives: The aim of our study was to evaluate the long-term functional outcomes between the Millin, Freyer, and Madigan RASP. Design: This is a single-center, retrospective evaluation of a prospectively maintained Institutional Review Board–approved database. Methods: Data from patients who have undergone RASP in our center were prospectively collected. Demographics, prostate size, and preoperative flowmetry parameters were assessed. Questionnaires such as International Index of Erectile Function (IIEF), and International Consultation on Incontinence Questionnaire (ICIQ), International prostatic symptoms score (IPSS) with its quality of life (QoL) score, Male Sexual Health Questionnaire (MSHQ), Overactive bladder questionnaire (OABQ) were administered to every patient preoperatively and during follow-up. We tested composite outcomes (trifecta) defined as a combination of postoperative Q-max >15 ml/s, IPSS score < 8, and absence of complications. We also tested a pentafecta which keeps in account the persistence of antegrade ejaculation (MSHQ > 0) and the erectile function maintenance (∆IEEF < 6). Results: Median follow-up was 36 months. Millin, Madigan, and Freyer procedures were performed in 37 (51%), 18 (25%), and 17 (24%) cases, respectively. Trifecta was achieved in 43 (60%) patients. Preoperative ICIQ, postoperative IPSS, postoperative OABQ, and QoL were significantly different between groups (all p < 0.02). Pentafecta was achieved by 14 (20%) patients. The pentafecta group showed a statistically significant advantage in terms of postoperative IPSS and MSHQ ( p < 0.01). Conclusion: RASP provides an effective and durable relief of obstructive symptoms at long-term follow-up, regardless of the technique, achieving the trifecta in the majority of the patients. The Madigan technique is significantly related to the pentafecta achievement.