Radical cystectomy (RC) is the primary treatment strategy for muscle invasive bladder cancer (MIBC). However, it carries a high risk of urethral recurrence (UR) in male patients. The risk factors and oncological outcomes of UR remain unclear. We aimed to identify the risk factors and oncological outcomes of UR in male patients with MIBC after RC combined with urinary diversion. After propensity score matching, we evaluated 137 male patients with MIBC who underwent RC combined with urinary diversion at our center between January 1, 2007 and December 31, 2015. Patient demographics, comorbidity, and perioperative data were recorded. Univariate and multivariate Cox proportional hazards regression were used to estimate the hazard ratio and 95% confidence intervals. Cancer-specific survival (CSS) and overall survival (OS) were measured using the Kaplan-Meier curve with log-rank test. P < 0.05 was considered statistically significant. Of the 310 patients, 30 (9.7%) patients underwent UR. In the matched group, the independent risk factors of UR were history of TURB (HR = 3.069, P = 0.018), tumor stage (T3 vs. T2, HR = 3.997, P = 0.014; T4 vs. T2, HR = 2.962, P = 0.015), and tumor multifocality (HR = 2.854, P = 0.011). The CSS and OS of patients with UR were equivalent to the patients without UR (P = 0.295, P = 0.616). This propensity score-matched case-control study showed that UR is not rare in male patients with MIBC after RC combined with urinary diversion. We identified three independent risk factors of UR: history of TURB, tumor stage, and tumor mutifocality. The oncological outcomes were equivalent between patients with and without UR. These findings could help improve treatment strategies and follow-up schedules.