Background & Objectives: Patients with bladder outlet obstruction (BOO) due to massive prostate enlargement have several surgical treatment options, such as robot-assisted simple prostatectomy (RASP) and holmium laser enucleation of the prostate (HoLEP). Postoperative outcomes may differ between those undergoing RASP and HoLEP. RASP has been associated with a lower incidence of transient stress urinary incontinence (SUI), while HoLEP allows for shorter catheterization times. Here, we report on our experience with both surgical modalities. Methods: Data were collected from prospectively maintained databases for 37 RASP patients and 181 HoLEP patients treated from July 2021 to November 2023. To control for selection bias, propensity score matching (PSM) was utilized based on age and prostate size. We compared patients preoperative, perioperative, and postoperative outcomes both before and after applying PSM. Results: Before the PSM, the median prostate size was significantly lower in the HoLEP group (p < 0.001). The HoLEP group also had significantly shorter operative times (p ≤ 0.001) and lower weights of resected adenoma (p ≤ 0.001). After the PSM of 31 RASP and 31 HoLEP patients, all baseline patient characteristics were comparable. No significant differences were observed in operation time (p = 0.140) or in the weight of resected adenoma (p = 0.394) between the modalities. The median (IQR) length of catheterization was significantly shorter in the HoLEP group (1 [1-4] days) compared to the RASP group (7 [7-8] days), in both pre- and post-matching analyses (p ≤ 0.001 for both), reflecting the standard of practice. In contrast, in both pre- and post-PSM analyses, the average hospital stay was significantly shorter in the RASP cohort, as same-day discharge is standard in our center, whereas the HoLEP cohort required overnight stays due to routine continuous bladder irrigation before discharge (p < 0.001 for all). Notably, the SUI rates and American Urological Association (AUA) symptom scores were comparable at 3 months within both matched and unmatched cohorts (pre-PSM: p = 0.668, p = 0.083; post-PSM: p = 1, p = 0.152, respectively). Conclusions: Our comparative analysis indicates that both RASP and HoLEP yield similar outcomes, including SUI rates, at 3 months. While HoLEP provided shorter durations of postoperative catheterization, RASP offered shorter hospital stays.