We report a rare case of Meckel's diverticulum in a boy who initially presented with chronic iron deficiency anemia (IDA) without any history of gastrointestinal (GI) bleeding at 8 years-old. Isolated small bowel Crohn's disease was suspected based on findings of small bowel ulcers on capsule endoscopy. At four years from initial presentation, he developed massive GI bleeding. Abdominal computed tomographic angiography and small bowel series revealed findings suggestive of Meckel's diverticulum. Meckel's diverticulum should be suspected in children with unexplained chronic IDA even in the absence of prominent GI bleeding and negative findings on repetitive Meckel's scans. Moreover, Meckel's diverticulum should be included in the differential diagnosis of isolated small bowel Crohn's disease when the disease is limited to a short segment of the distal small bowel, as ulcers and inflammation may result as a consequence of acid secreted from adjacent heterotopic gastric mucosa constituting the Meckel's diverticulum.