Background: Percutaneous biliary balloon dilation (PBBD) stands as a safe, useful, and inexpensive treatment procedure performed on patients with benign anastomotic stricture of Roux-en-Y hepatojejunostomy (BASH). However, the optimal mode of application is still under discussion. Methods: A retrospective cohort study was conducted including patients admitted between 2008 and 2015 with diagnosis of BASH. Patients were divided into 2 groups: group I (n = 22), included patients treated after the implementation of an institutional protocol of 3 PBBD sessions within a fixed time interval and group II (n = 24) consisted of our historical control of patients who underwent one or 2 dilation sessions. Patency at one-year post procedure was assessed with the classification proposed by Schweizer. Symptomatic response to treatment was analyzed using the Terblanche classification. Results: Patients in group I exhibited more excellent/good results (90 vs. 50%, p = 0.003) and less poor results (5 vs. 42%, p = 0.005) according to the Schweizer classification and more grade I/excellent results according to Terblanche classification (p = 0.003). Additionally, group I showed lower serum total bilirubin (p = 0.001), direct bilirubin (p = 0.002), alkaline phosphatase (p = 0.322), aspartate aminotransferase (p = 0.029), and alanine aminotransferase (p = 0.006). Conclusion: A protocol of 3 consecutive PBBD sessions within a fixed time interval may yield a high rate of patency, with a positive clinical, biochemical, and radiological impact on patients with BASH.