BackgroundThere have been few studies of countermeasures against postoperative cholangitis, a serious complication after pancreaticoduodenectomy (PD) that impairs quality of life.ObjectiveTo evaluate our recently developed, novel method of choledochojejunostomy with a larger anastomotic diameter, the “T‐shaped anastomosis.”MethodsThe study included 261 cases of PD. The T‐shaped choledochojejunostomy technique was performed with an additional incision for a distance greater than half the diameter of the bile duct at the anterior wall of the bile duct and the anterior wall of the elevated jejunum. To compensate for potential confounding biases between the standard anastomosis group (n = 206) and the T‐shaped anastomosis group (n = 55), we performed propensity score matching (PSM). The primary endpoint was the incidence of medium‐term postoperative cholangitis adjusted for PSM.ResultsIn the PSM analysis, 54 patients in each group were matched, and the median bile duct diameter measured by preoperative CT was 8.8 mm versus 9.3 mm, the rate of preoperative biliary drainage was 31% versus 37%, the incidence of cholangitis within 1 month before surgery was 9% versus 13%, and the incidence of postoperative bile leakage was 2% versus 2%, with no significant differences. The incidence of medium‐term postoperative cholangitis was 15% versus 4%, and multivariate logistic regression revealed that T‐shaped choledochojejunostomy was an independent predictor of a reduced incidence of cholangitis (odds ratio, 0.17, 95% CI 0.02–0.81; p = 0.024).ConclusionsThe T‐shaped choledochojejunostomy technique was shown to be effective with a significant reduction in the incidence of medium‐term postoperative cholangitis. Clinical trial identification: UMIN000050990.