Gastric duplication cysts (GDCs) are rare congenital anomalies. Presentation of GDCs varies from an asymptomatic abdominal mass to fulminant or massive gastrointestinal (GI) bleeding. Herein, we describe a case of a GDC in a 10-month-old infant presenting with unexplained massive GI hemorrhage and hematemesis. An abdominal ultrasound was negative, while computerized tomography was, initially, inaccessible. Through a series of repeated esophagogastroduodenoscopies, we documented penetration of the GDC into the gastric cavity that was later confirmed by computerized tomography. The patient was treated successfully with surgical resection.