Introduction: Benign uretero-ileal anastomotic stricture is a significant complication following radical cystectomy and ileal conduit urinary diversion after radical cystectomy. We examined risk factors for stricture formation to predict those at greatest stricture risk. Methods: A retrospective chart review was conducted for patients undergoing radical cystectomy and ileal conduit diversion between 2002 and 2012. Demographic data and patient variables were analyzed to determine risk factors for uretero-ileal stricture using multivariate logistic regression. Results: Over the study period, 133 patients underwent cystectomy and ileal conduit formation, with 14 (10.5%) developing ureteroileal anastomotic stricture. Diabetes and elevated serum urea level (defined as >7.1 mmol/L) were associated with increased risk for development of uretero-ileal stricture (odds ratio 4.31 and 4.28, respectively; p<0.05 for each). Conclusions: In this patient cohort, diabetes and elevated serum urea level were predictive for the development of uretero-ileal anastomotic stricture. Further prospective study with larger patient samples is required.