Meckel's diverticulum is a common congenital anomaly found in ∼2% of the population, its classic location aiding in its diagnostic criteria, is the anti-mesenteric side of the distal ileum. However, reported cases of Meckel's diverticula found on the mesenteric side, are present but rare. Here we report a case of a perforated mesenteric Meckel's diverticulum with synchronised anti-mesenteric Meckel's diverticulum, in a 70-year-old male, initially misdiagnosed as left strangulated inguinal hernia. The purpose behind this paper is to raise clinical suspicion regarding this rare pathology, so that timely diagnosis and management could be carried out.