A 33-year-old postpartum patient, who had an uncomplicated repeat caesarean section 4 weeks prior, presented with a 2-day history of acute right lower quadrant, incisional and groin pain. She was found to have a palpable tender lump in the right groin. A CT scan with contrast identified fluid along the anterior abdominal wall of the right lower quadrant (inguinal region) measuring about 1.7 cm, a preliminary diagnosis of an incarcerated inguinal hernia was made and the patient underwent immediate surgery. The hernia sac was dissected free and had chocolate cyst that was confirmed to be endometrioma on histopathology. The hernia defect was repaired. Postoperative, the patient did well and was discharged home. We emphasise to consider this differential diagnosis of extrapelvic inguinal endometrioma in reproductive-aged women with or without history of endometriosis especially in a post-caesarean patient who has atypical presentations.