It has been reported that intrathoracic esophageal leakages occur at a rate of 4%–17% after Ivor-Lewis esophagectomy. There has been no consensus on a specific treatment for the post-operative anastomotic leakage. Recently, endoscopic vacuum-assisted closure (E-VAC) has been introduced as a novel treatment for the post-operative anastomotic leakage. We herein report the case of a patient with early perforation of the gastric conduit followed by late esophagogastric anastomotic leakage who was successfully treated with early surgical repair and subsequent E-VAC. The patient had been previously diagnosed with achalasia and squamous cell carcinoma of the esophagus and undergone an Ivor-Lewis esophagectomy.