Internal hernia is an uncommon cause of acute abdominal pain and accounts for 0.2-0.9% of intestinal obstruction. Internal herniation through the Foramen of Winslow (FW) is extremely rare, approximately 0.08% abdominal hernias. In this case report, we demonstrate a rare finding of internal herniation involving Meckel’s diverticulum through the Foramen of Winslow. The established incarceration of small bowel within the Foramen of Winslow precluded pure laparoscopic reduction of the hernia. The hernia was reduced with the use of Hand-assisted Laparoscopic surgery (HALS) via a Gelport to avoid converting to laparotomy. This adds knowledge to the management of rare internal hernia cases in our current literature.