Esophagitis dissecans superficialis (EDS) is described as the peeling of squamous mucosa of the esophagus with regurgitation of esophageal casts. It is a rare endoscopic finding associated with chemical irritants, autoimmune disorders, or medications. Most patients are asymptomatic but clinical manifestations can include dysphagia, heartburn, bleeding, or vomiting. In this report, we present a case of a 70-year-old man with a previous history of small cell lung and hepatocellular carcinoma for which he had undergone chemoradiation and immunotherapy. He had presented with upper gastrointestinal hemorrhage manifested as coffee ground emesis. Endoscopic findings were consistent with EDS. No recurrence of his gastrointestinal hemorrhage was observed after acid-suppressive therapy. With our case report, we aim to increase awareness for EDS as a differential diagnosis for gastrointestinal hemorrhage.