This study aimed to determine the occurrence and grade of cystographically detected urinary leakage (UL) in a contemporary series of open retropubic radical prostatectomy (RP), whether patients' clinical variables predict occurrence of UL, and whether occurrence of UL correlates with patients' voiding outcomes in terms of urinary continence and anastomotic stricture (AS). Enrolled patients underwent cystography 7 days after retropubic RP; in case of UL, the catheter was left in situ and cystography repeated at 7 days intervals until demonstrating absence of UL. Leakage was classified as grade I = extraperitoneal leak <6 cm, grade II = extraperitoneal leak >6 cm, grade III = leak freely extending in the small pelvis. Voiding was evaluated at 3, 6, and 12 months after RP using the 24-hour pad test and uroflowmetry; in cases of maximum flow rate <10 mL/s, urethrocystoscopy was carried out to determine presence and location of an AS. The first postoperative cystogram showed UL in 52.6% of patients (grade I in 48.1%, grade II in 21.5%, and grade III in 30.4% of the cases). Multivariate analysis demonstrated that patients with UL had significantly greater prostate volume (64.5 vs 34.8 cc, P < 0.001), loss of serum hemoglobin (4.77 vs 4.19 g/dL, P < 0.001), lower postoperative serum total proteins (4.85 vs 5.4 g/dL, P < 0.001), and higher rate of AS (20.6% vs. 2.8%, p < 0.001) than those without UL. Continence rate at 3, 6, and 12 months postoperatively was 34.2%, 76%, and 90%, respectively, in patients with UL compared with 77.5%, 80.3%, and 93% in patients without UL; such difference was statistically significant (P < 0.001) only at 3 months follow-up. ROC curve analysis showed that prostate volume and postoperative serum total proteins had the best AUC (0.821 and 0.822, respectively) and when combined, their positive and negative predictive values for UL were 90% and 93%, respectively. In conclusion, half of the patients undergoing open retropubic RP may present, 7 days postoperatively, some degree of cystographically detected UL; prostate volume, loss of serum hemoglobin, and postoperative serum total proteins could be used to predict it. UL delayed return to urinary continence without affecting long-term results, but led to a significantly higher rate of AS.