Introduction: Delayed massive bleeding from an ischemic ulcer is a complication after Roux-en-Y gastric bypass (RYGB). Ischemic ulcers that present with massive bleeding are rare and challenging for the gastroenterologist as well as the bariatric surgeon. Case Description: This report reviews the case of a 63-year-old man who underwent an uncomplicated laparoscopic RYGB for morbid obesity and experienced two episodes of massive hemorrhage after the procedure, almost 1 year apart. Conclusion: To our knowledge, there are only a few such specific cases reported. Here, we describe the treatment and outcome for such a case and present a review of the literature.