Background and objectives: Concomitant biliary and duodenal malignant obstruction are a severe condition mainly managed by duodenal and biliary stenting, which can be performed simultaneously (SAMETIME) or in two distinct procedures (TWO-TIMES). We conducted a single-center retrospective study to evaluate the feasibility of a SAMETIME procedure and the impact of endoscopic ultrasound (EUS)-hepaticogastrostomy in double malignant obstructions. Patients and methods: From January 1, 2011, to January 1, 2018, patients with concomitant malignant bilioduodenal obstruction treated endoscopically were included. The primary endpoint was hospitalization duration. The secondary endpoints were bilioduodenal reintervention rates, adverse event rates, and overall survival. Patients were divided into groups for statistical analysis: (i) divided according to the timing of biliary drainage: SAMETIME vs. TWO-TIMES group, (ii) divided based on the biliary drainage method: EUS-HG group underwent hepaticogastrostomy, while DUODENAL ACCESS group underwent endoscopic retrograde cholangiopancreatography (ERCP), percutaneous transhepatic drainage (PCTD) or EUS-guided choledocoduodenostomy (EUS-CD). Results: Thirty-one patients were included (19 women, median age = 71 years). Stenosis was mainly related to pancreatic cancer (17 patients, 54.8%). Sixteen patients were in the SAMETIME group, and 15 were in the TWO-TIMES group. Biliary drainage was performed by EUS-HG in 11 (35.%) patients, PCTD in 11 (35.%), ERCP in 8 (25.8%) and choledoduodenostomy in 1. Thirty patients died during follow-up. The median survival was 77 days (9% confidence interval [37-140]). The mean hospitalization duration was lower in the SAMETIME group: 7.5 vs. 12.6 days, P = 0.04. SAMETIME group patients tended to have a lower complication than TWO-TIMES (26.7% vs. 56.3%, P = 0.10). The EUS-HG group tended to have a lower complication rate (5% vs. 18.2%, P = 0.07) and less biliary endoscopic revision (30% vs. 9.1%, P = 0.37) than DUODENAL ACCESS. Conclusions: SAMETIME drainage is associated with a lower hospital stay without increased morbidity. EUS-HG could provide better access because it did not exhibit a higher complication rate and showed a tendency toward better patency and fewer complications.