Groove pancreatitis, a form of chronic pancreatitis affecting the head of the pancreas, is localized within the groove between the pancreas head, duodenum, and common bile duct. We report a case of a male patient with groove pancreatitis who initially underwent a duodenal preserving gastrenteranastomosis. Unfortunately, the patient's symptoms were only partially controlled, necessitating a pancreaticoduodenectomy in due course as the definite surgical restoration procedure. The surgical approach selected proved inadequate since the patient's symptoms did not resolve over time. This reflects that by-pass operations like these are not indicated for the management of patients with groove pancreatitis.