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Prior transurethral resection of the prostate (TURP) may distort bladder neck and apical anatomy and complicate robot-assisted radical prostatectomy (RARP). Its effect on anastomotic recovery and oncological control remains controversial. To evaluate perioperative, anastomotic, pathological, and available PSA outcomes after RARP in patients with and without prior TURP. We retrospectively analyzed a prospectively maintained database of 3,332 consecutive RARP procedures performed between August 2011 and December 2024. Ninety-seven patients with prior TURP were matched 1:3 to 291 TURP-naive controls using propensity scores derived from age, body mass index, clinical stage, ISUP grade, prostate-specific antigen (PSA), positive biopsy cores, and prostate volume. Comparative outcome analyses used available cases within the matched cohort. Baseline characteristics were well balanced after matching. Operative duration was similar between groups (median 135 vs. 139 min; p = .584). Prior TURP was associated with longer catheterization (7 [IQR 4.5-11.5] vs. 6 [4-7] days; p = .004), more cystographies (p = .004), more frequent catheterization beyond 7 days (33.7% vs. 20.1%; p = .011), and a higher rate of complications within 3 months (13.4% vs. 6.2%; p = .030). Cystographic leakage was numerically more frequent after TURP (25.4% vs. 14.8%; p = .061). Pathological stage, nodal positivity, positive surgical margin rate and length, and available PSA outcomes at 1 and 2 years were comparable. After Bonferroni adjustment, catheterization duration and the number of cystographies remained statistically significant. Prior TURP was associated primarily with greater postoperative anastomotic management reflected by longer catheterization and more cystographic follow-up; the observed increase in 3-month complications did not remain significant after correction for multiple comparisons. Available PSA data did not indicate a clear between-group difference, although incomplete follow-up precluded robust conclusions regarding biochemical control.