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The surgical outcome of middle and/or distal bile duct cancer remains unsatisfactory. Although the resectional margin is known to be a predictive factor, the prognostic significance of a positive ductal margin and other radial margin has never been evaluated independently.The clinicopathologic data of 55 patients who had undergone surgical resection for middle and/or distal bile duct cancer between 1987 and 2003 were reviewed retrospectively. The surgical procedures consisted of pancreatoduodenectomy in 42 patients (76%), extrahepatic bile duct resection in 8 patients (15%), major hemihepatectomy (Hx) in 3 patients (5%), and pancreatoduodenectomy plus Hx in 2 patients (4%). In all the patients, intraoperative diagnosis of the ductal margins was performed using frozen sections. Twenty-one clinicopathologic factors, including the status of the ductal margins and of other radial margins, were evaluated using univariate and multivariate analyses.The overall 5-year survival rate and the median survival time were 24% and 38 months, respectively. There were 4 (7%) postoperative deaths. Fifteen of the remaining 51 patients (29%) were determined to have positive hepatic-side ductal margins during operation, and 14 of them underwent additional resection of the bile duct (1.6[range, 1–3] times, on average). As a result, hepatic-side ductal margin (hm) and duodenal-side ductal margin were found to be positive in 6 and 0 patients on the final pathologic analysis, respectively. Two of the 6 patients (33%) with positive hm have developed ductal recurrence so far, but the status of hm was not found to be a significant predictor. The depth of neoplastic invasion into the bile duct wall, pancreatic invasion, radial margin, and blood transfusion were significant prognostic factors by the univariate analysis. Multivariate analysis revealed that the depth of neoplastic invasion and blood transfusion were the independent prognostic factors.In the treatment of middle and distal bile duct cancer, it is of importance to secure a negative radial margin, although it may be less beneficial to obtain a negative hm. Surgeons should make efforts to obtain negative radial margins and to avoid blood transfusion.