Neonatal gastric perforation (NGP) is a life-threatening condition associated with high morbidity and mortality rates. Despite several proposed etiological theories, the causative principle is still unclear and controversial. A male neonate was born at 26 weeks 3 days gestation. The patient showed symptoms of acute respiratory failure and hypoxia and was admitted to the neonatal intensive care unit. On day of life (DOL) 2, a chest and abdominal radiography showed a large amount of free intraperitoneal air, for which exploratory laparotomy was performed. A small antimesenteric perforation in the distal ileum was found and repaired primarily. On DOL 7, a chest and abdominal radiography demonstrated recurrent pneumoperitoneum for which a repeat exploratory laparotomy was performed. The patient had global intestinal ischemia and a perforation in the anterior wall of the stomach, which was repaired. On DOL 12, a planned upper gastrointestinal water-soluble contrast study showed spillage of contrast into the anterior abdomen, for which the patient underwent a repeat exploratory laparotomy. We found a dehiscence of the prior gastric repair and closed it primarily. The remainder of the hospital course was uneventful and the patient reached full feedings on DOL 41. Premature neonates are at risk for gastric perforation. Gastric perforation should be in the differential diagnosis of a premature neonate who presents abdominal distension and pneumoperitoneum. Due to the fragility of the premature neonatal tissues, confirming the integrity of the gastric closure with a contrast study is recommended prior to initiating enteral feedings.