A 34-year-old female presented with colicky abdominal pain and symptoms suggestive of subacute small bowel obstruction in the setting of Crohn's disease (CD). She was on maximal medical therapy and had undergone endoscopic balloon dilatation of a terminal ileal stricture on two occasions. Magnetic resonance enterography demonstrated acute inflammation in two segments of the terminal ileum. The patient proceeded to laparoscopic ileocolic resection. The histopathology revealed a segment of stricturing CD with chronic inflammatory change. There was also an unexpected finding of a segment of stricturing ileal disease secondary to endometriosis. Endometriosis affecting the ileum is uncommon, and concurrent CR and endometriosis is very rare. Further research is required to understand whether these two conditions are associated. Here, we present a discussion on the histopathology differences between endometriosis and CD. Clinicians are reminded of these rare concurrent conditions, as the symptomatology may mimic one another, thus impacting the treatment and management.