Surgical treatment of symptomatic benign prostatic hyperplasia (BPH) has seen an evolution during the last decades. On one hand, en-bloc HoLEP emerged as a valid endoscopic treatment regardless prostate size. On the other hand, robot-assisted simple prostatectomy (RASP) has gained attention in larger prostates showing encouraging results. Herein, for the first time in the scientific scenario, we sought to compare the outcomes of RASP and en-bloc HoLEP cases after propensity-score matching (PSM) analysis. We retrospectively queried our prospectively database of patients treated with HoLEP or RASP between 2017 and 2022 among two high-volume centers. PSM was applied based on the International Prostate Symptom Score (IPSS) questionnaire, prostate volume and max-flow rate. All procedures were performed by a single surgeon per center. Outcomes were assessed at 1, 3, and 6-month postoperatively and therefore annually. Trifecta definition was used to assess "success" in surgical procedures and was defined as the contemporary presence of: a) no postoperative complications within the first postoperative month; b) 1-month postoperative Qmax >15 ml/s and c) no urinary incontinence at 3-month evaluation. Overall, 48 HoLEP and 47 RASPs were matched. Operative time, hospitalization time (median 4 vs 5 days) and catheterization time (median 3 vs 2 day) were found to be shorter in the HoLEP group as compared to the counterpart (p < 0.05). Early postoperative complication rate was also lower in the HoLEP cohort (6.2% vs 12.6%; p = 0.03) as well as postoperative haemoglobine blood level drop (1.4 vs 2.4 g/dL; p = 0.03). On the other hand, postoperative antegrade ejaculation (55.3% vs 6.8%) 1-month max flow (median 28 vs 24 ml/sec) and continence rates (0% vs 20.8%) favored RASP (p < 0.05). Overall, Trifecta rate was similar in the two groups (76.1% vs 82.6%). Both HoLEP and RASP are safe and effective treatments for symptomatic BPH. HoLEP demonstrated to have lower perioperative risks while is affecting by a higher probability of transient early UI. On the other hand, RASP is more effective in reducing postoperative ejaculatory dysfunction.