Introduction: An esophagojejunal anastomotic leak following an oncological gastrectomy is a life-threatening complication, and its management is challenging. A stent application and endoscopic negative pressure therapy are possible therapeutic options. A clinical comparison of these strategies has been missing until now. Methods: A retrospective analysis of 14 consecutive patients endoscopically treated for an anastomotic leak after a gastrectomy between June 2014 and December 2019 was performed. Results: The mean time of the diagnosis of the leakage was 7.14 days after surgery. Five patients were selected for a covered stent, and nine patients received endoscopic negative pressure therapy. In the stent group, the mean number of endoscopies was 2.4, the mean duration of therapy was 26 days, and the mean time of hospitalization was 30 days. In patients treated with endoscopic negative pressure therapy, the mean number of endoscopies was 6.0, the mean days of therapy duration was 14.78, and the mean days of hospitalization was 38.11. Treatment was successful in all patients in the stent-based therapy group and in eight of nine patients in the negative pressure therapy group. Discussion: Good clinical results in preserving the anastomosis and providing sepsis control was achieved in all patients. Stent therapy resulted in anastomosis healing with a lower number of endoscopies, a shorter time of hospitalization, and rapid oral nutrition.