Gross perforation of sigmoid diverticulitis is usually managed by sigmoid colectomy. We present a unique case of a 70-year-old male who presented to our hospital with grossly perforated sigmoid diverticulitis within a strangulated left inguinal hernia. The patient did not have any clinical signs of intra-abdominal sepsis, and only a groin abscess on computed tomography. Diagnostic laparoscopy revealed absence of abdominal contamination; only the herniation of two large sigmoid diverticula into the left groin. Sigmoid diverticulectomy was performed, and a drain was placed into the abdominal cavity. The groin abscess was then externally incised and drained, and the two perforated diverticula retrieved through the groin incision without any gross intra-abdominal contamination.