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Gastric cancer surgery has evolved considerably over the past years, with substantial improvement on outcomes. Meanwhile, esophagojejunal anastomotic fistula (EJF) continues to impair postoperative results. This study aimed to assess EJF regarding its incidence, risk factors, management and the impact on overall survival. We retrospectively analyzed 258 consecutive patients who underwent total or completion gastrectomy for GC from 2009 and 2017. Clinicopathological characteristics analysis was performed comparing patients who developed EJF with patients with other clinical or surgical complications, as well as patients without any postoperative complications. Fifteen (5.8%) patients had EJF and 81 (31.4%) had other complications (including other surgical fistulas). The median time of EJF diagnosis was on the eighth postoperative day (range 3-76). Completion gastrectomy (p = 0.048) and longer hospital stay (p < 0.001) were associated with the occurrence of EJF. The surgical mortality of patients with EJF was higher than in non-EJF patients (26.7% vs. 4.5%; p < 0.001). Nine patients were treated conservatively and six required surgery. The mortality rate of EJF was 11.1% and 50% in patients who underwent conservative and surgical treatment, respectively. Patients with other complications and patients with EJF had worse survival compared to patients without any complication (p = 0.004 and p = 0.013, respectively). Completion gastrectomy is the main risk factor for EJF occurrence. Still, EJF is associated with high postoperative mortality, longer hospital stay and has a negative impact on long-term survival.