BackgroundAlthough intraductal plastic stent (IS) placement is an effective treatment for unresectable malignant hilar biliary obstruction (UMHBO), the effectiveness of unilateral and bilateral IS drainage remains controversial. This retrospective study investigated the effectiveness of bilateral IS placement for UMHBO using the propensity score matching method.MethodsPatients who underwent transpapillary endoscopic stenting for UMHBO were analyzed for technical and clinical success, adverse events, and time to recurrent biliary obstruction (TRBO).ResultsA total of 321 patients were enrolled in the study with 27 patients in each unilateral and bilateral IS group in the propensity score‐based cohort. Technical success was 100%, while clinical success was 93% and 96% in the unilateral and bilateral IS groups, respectively (p = 1.0). Cholecystitis occurred in 4% and 7%, respectively (p = 1.0). The median TRBO was shorter in the unilateral group (129 [5–383] days) than that in the bilateral group (226 [16–563] days) (p = .0281). Bilateral IS placement was an independent long TRBO factor (hazard ratio [HR] 0.46; 95% confidence interval [CI]: 0.21–0.97; p = .041).ConclusionsUnilateral and bilateral IS placement had high technical and clinical success rates in primary stent placement. However, bilateral IS placement showed a longer TRBO. Bilateral IS placement may be a good option for initial UMHBO drainage.