Groove pancreatitis is a rare form of segmental chronic pancreatitis. It involves the anatomic space between the head of the pancreas, the duodenum and the common bile duct. It was first described in the early 1970s, but it remains largely unfamiliar to most physicians. Radiological diagnosis can be challenging, as it is often difficult to differentiate it from other entities. The differential diagnosis from pancreatic head carcinoma may be difficult and recognition of subtle differences between these two entities is extremely important as the management differs significantly. Groove pancreatitis can be managed by conservative medical treatment, and surgery is reserved only for patients with persistent and severe clinical symptoms. We present a case of a 27 year-old male with groove pancreatitis and discuss the Magnetic Resonance Imaging (MRI) appearance of this entity as well as the differential diagnosis.