Postoperative enteroenteric intussusception is a rare complication in adult patients with Crohn's disease. We treated two patients with Crohn's disease accompanied by an ileal obstruction, each of whom underwent an elective resection. In both, the upper left quadrant of the abdoment became progressively distended following ileocecal resection and each required surgical treatment after diagnosis of postoperative enteroenteric intussusception by abdominal computed tomography scanning, as the intussusception could not be reduced by conservative treatment. There were no Crohn's lesions found in the intussuscepted specimens, and the condition was thought to have been caused by a segment of thickened and fibrotic intestine that had developed because of long-standing bowel dilatation from obstructive Crohn's lesions. In one of the patients, the intussusceptum was irreducibly incarcerated and required a resection, whereas it was able to be manually reduced in the other.