Benign bile duct stricture (BBS) can lead to recurrent cholangitis, biliary cirrhosis, hepatic failure, and death if untreated. Although excellent outcomes can be achieved by Roux-en-Y hepaticojejunostomy (RYHJ), in the majority of patients with BBS, a subset of patients can have recurrent anastomotic site strictures requiring revision Roux-en-Y hepaticojejunostomy (rRYHJ). This study is a review of patients undergoing revision Roux-en-Y hepaticojejunostomy. Case series analysis of retrospective data from patients undergoing rRYHJ from January 1989 to December 2020 was conducted. Their demographic, preoperative, intraoperative, and postoperative outcomes were analyzed. A total of 44 (6.98%) patients had recurrent anastomotic site strictures among 630 patients who had undergone RYHJ (Roux-en-Y hepaticojejunostomy) for benign biliary stricture following bile duct injury at a minimum follow-up of 3 years. Among 44 patients, 36 patients (81.8%) underwent rRYHJ (revision Roux-en-Y hepaticojejunostomy). Their mean age was 48.5 years, and the majority were women with 26 (59%) of the patients. The mean duration between primary (RYHJ) and revision (rRYHJ) was 5.5 years. Thirty-two (88.8%) patients presented with cholangitis, and one patient (2.7%) had cirrhosis. Twenty-four (75%) patients underwent preoperative biliary drainage. Types of re-strictures (on the basis of intraoperative assessment) according to bismuth classification included type I 1 (2.78%), type II 3 (8.3%), type III 20 (55.5%), type IV 10 (27.8%), and type V 2 (5.5%). Twelve patients (33%) had postoperative complications, and the most common complication was surgical site infection (n = 8, 22.2%). There was no mortality. Two patients had postoperative bile leakage, managed conservatively (Clavien-Dindo (CD) grade I). On long-term follow-up (mean 5.5 years), satisfactory outcomes (A and B McDonald's grade) were observed in 31 (86%) patients, 3 (8.3%) patients had grade C outcomes, and 2 (5.5%) patients had grade D outcomes. Overall, 29.5% (13) of cases, including 6 cases of bile duct stricture after the first RYHJ and 5 cases of re-stricture after revision r-RYHJ, were managed successfully with balloon dilation and ring biliary catheter, showing better long-term outcomes. Our study has shown that the overall post-revision Roux-en-Y hepaticojejunostomy (rRYHJ) long-term outcome was satisfactory in 86% of patients according to McDonald's grading. A multidisciplinary approach in high-volume center is paramount important to obtaining a good long-term outcome.