Introduction: Obstructive jaundice is a common problem in pancreatic and periampullary tumors, but preoperative biliary drainage in patients with hyperbilirubinemia is still controversial. This study aimed to assess the risk of complications after preoperative drainage of biliary obstruction in patients who underwent pancreaticoduodenectomy. Method: A retrospective cohort study of all patients who underwent pancreaticoduodenectomy from January 1st, 2015 to September 30th, 2021. Patients who had preoperative bile duct drainage were compared to patients without intervention. Type of interventions, complications, and outcomes after surgery were compared using univariate and multivariate analysis. Results: Of 722 patients who underwent pancreatoduodenectomy, 389 patients had preoperative drainage of the bile ducts by ERC or PTC. There was an incidence of 27% drainage-related complications, all categorized as minor (Clavien-Dindo <3) and mainly related to PTC-aided drainage. After pancreaticoduodenectomy, 23% of patients who had a preoperative biliary drain, had minor complications. Patients without biliary drainage had a higher risk of a complicated postoperative course (p = 0.001) and had a higher 30-day (p = 0.002) and 90-day mortality (p = 0.025). Conclusion: Our study found preoperative bile duct drainage to be a safe procedure without severe complications. Patients undergoing preoperative bile duct drainage had fewer post-pancreatoduodenectomy complications and lower mortality.