This study aims to provide a deep insight into the incidence and clinical significance of postoperative anastomotic leakage (AL) and anastomotic stenosis (AS) of the hepaticojejunostomy (HJ) after curative-intent liver resection for perihilar cholangiocarcinoma (pCCA). Between 2011 and mid-2019, 114 patients with pCCA underwent surgery in curative intent at our institution and were analyzed regarding the postoperative incidence of AL and AS. Further, associations between AL and AS and clinical characteristics were assessed using multiple univariate logistic regression analyses. AL was diagnosed in 11.4% (13/114) of the patients resulting in postoperative mortality in the minority of patients (23.0%, 3/13). AS occurred in 11.0% (11/100) of the individuals eligible for follow-up with local tumor recurrence being the underlying pathology in 72.7% (8/11) of the cases. None of the investigated clinical factors including surgical difficulty of the HJ showed a meaningful association with AL or AS. AL and AS are frequent complications and can be treated by conservative, interventional or surgical therapy with a high success rate. Also, technical difficulty of the HJ appears not to be not associated with the occurrence of AL or AS. Moreover, AS is associated with tumor recurrence in the majority of cases.