The pain in the right iliac fossa corresponds with many clinical conditions, most commonly Acute appendicitis. Rarely peptic ulcer perforation presents as pain in the right iliac fossa. This condition is called as Valentino’s syndrome. This is due to the leakage of the gastric contents from the stomach or duodenum during the perforation. This induces peritonitis and sometimes the fluids get collected in the right iliac fossa causing pain, hence mimicking appendicitis. This is the case study of a 17yr old boy with right iliac fossa pain and tenderness, vomiting, fever, all corresponding to acute appendicitis. But on surgical exploration, it was found to be duodenal perforation. Valentino’s syndrome is a very misleading condition which will lead to death if proper evaluation and timely management is not done. This study emphasis the fact that Valentino’s syndrome has to be considered as the differential diagnosis in symptoms suggestive of acute appendicitis.