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BACKGROUND AND AIM Self-expandable metallic stents (SEMSs) are widely accepted as a less-invasive treatment for malignant gastric outlet obstruction (GOO). However, the factors related to prognosis and stent dysfunction after SEMS placement are not well known, and we aimed to investigate them. METHODS This was a single-center retrospective cohort study of 212 malignant strictures in 207 patients. Factors related to prolonged overall survival (OS) and time to recurrent GOO (TRGOO) after SEMS placement were evaluated. RESULTS Improvement of oral intake was confirmed in 179 patients (86%). The median OS was 65 days. A Cox proportional hazards model revealed that lower cancer stage, lower performance status score at the time of SEMS placement, and administration of chemotherapy after SEMS placement were significant predictive factors for prolonged OS. The median OS was 182 days in the group of SEMS followed by chemotherapy (group A) and 43 days in the group of SEMS alone (group B) (p< .0001). Chemotherapy after SEMS implantation contributed to the prolongation of survival in gastric cancer (hazard ratio (HR), 0.12) and pancreatic cancer (HR, 0.41). Furthermore, the cumulative incidence rates of stent dysfunction on day 120 after SEMS placement were 30% in group A and 61% in group B (p=.03). Notably, the preventive effect of chemotherapy on stent dysfunction was significant in pancreatic cancer. CONCLUSIONS SEMS is a treatment with high technical and clinical success rate for malignant GOO. Furthermore, subsequent chemotherapy prolongs OS especially in gastric cancer, and TRGOO in pancreatic cancer.