A jejunal diverticulum is a rare and usually asymptomatic disease. More commonly it is usually seen as incidental findings on radiological studies or during surgery. Complications such as bleeding, perforation, abscess formation, obstruction, malabsorption, blind loop syndrome, volvulus, and intussusception may warrant surgical intervention. Herein, we report a case of a 62-year old woman presenting with massive lower gastrointestinal bleeding, she was pale, clammy and hemodynamically unstable, she was initially resuscitated with IV fluids and whole blood, urgent upper endoscopy was normal, colonoscopy revealed sigmoid colon ulcerative lesion with histopathological evidence of adenocarcinoma, there was bleeding coming from upwards. After staging of the tumor, the decision was then made to proceed to exploratory laparotomy with a pre-operative plan of segmental colectomy. Intra-operatively segmental sigmoid colectomy was performed with end to end anastomosis, during formal laparotomy we found 2 giant diverticula in the proximal jejunum, small bowel resection and end to end anastomosis was done with the good postoperative outcome. The aim of this study was to draw attention to jejunal diverticula and their serious complications such as bleeding.