The duodenum is the most common extra-colonic site of diverticulum. If present, it rarely manifests with symptoms or complications. A case is discussed involving a 78-year-old female who presented with massive upper gastrointestinal bleeding from duodenal diverticula. Due to hemodynamic instability, she eventually underwent duodenal resection, with a side-to-side duodenojejunostomy as a means of restoring intestinal continuity. The postoperative course was unremarkable. The patient was able to feed enterally and had no recurrence of bleeding.