Background: Intestinal anastomosis is one of the most commonly performed surgical procedures, especially in the emergency setting and is also commonly performed in the elective setting when resections are carried out for benign or malignant lesions of the gastrointestinal tract. Anastomotic leak after gastrointestinal anastomosis is one of the important postoperative complication that leads to significant morbidity and adversely affects length of hospital stay. Objective: To define the risk factors, presentation and outcome of anastomotic leakage after gastrointestinal anastomosis. Methods: Prospective data collection from patients who underwent small or large bowel resection and anastomosis without fecal diversion in the surgical department in Al Zahraa University Hospital in the period between November 2010 and April 2014. Demographic details of the patients as well as preoperative, intraoperative and postoperative data were recorded. Leak found or not and on which postoperative day leak found. How it was identified (clinical or radiological) and how it was treated. Outcome of patients was recorded as mortality rate and postoperative hospital stay.   Results: There were 70 (63.64%) males and 40 (36.36%) female patients. Mean age was (44.23 ± 15.78) years. Anastomotic leak was occurred in 17 (15.4%) patients group I, while there was no leak in 93 patients (84.6%) group II. The mean postoperative period for diagnosis of anastomotic leakage was 9 days range (5-16) days. Categorical variable found to be significantly affecting the outcome of anastomosis were age of the patients (P£0.001), smoker versus nonsmoker (P£0.0001), preoperative chemotherapy, radiation and anti T.B. (P£0.001), type of surgery elective versus emergency (P£0.05). Bowel preparation done in 73 versus not done in 37 (P£0.05), level of anastomosis small bowel and choledocojejunostomy versus gastrojejunstomy and large bowel (P£0.001), left versus right side colonic anastomosis (P£0.05). Intraoperative blood loss (P£0.0001). Blood transfusion >2 unit (P£0.0001).   Mortality rate was (29.41%) 5/17 in group I, while it was (3.23%) 3/93 in group II. The postoperative hospital stay was (24.7 ± 5.92) days in group I, while for group II it was (12.83 ± 3.8) days.   Conclusion: Postoperative gastrointestinal anastomotic leak is a very serious complication that has great clinical impact on patients, putting surgeons in dilemmas of detection and management. There is multiple risk and predictive factors associated with occurrence of leak were suspected in this study such as: older patients, preoperative anemia, hypoalbuminemia, immunosuppressive therapy, smoking, surgery performed in an emergency setting, without adequate bowel preparation, long operative time, intraoperative blood loss and blood transfusion and low pelvic anastomosis, but many factors remain unclear. The presentation of anastomotic leakage varying from severe peritonitis and leakage of bowel content through the wound or from the drain to asymptomatic (small pelvic abscess).   Early detection and expediently treatment is very helpful to improve the patients outcome but death after leak is most often a substitute for a critically ill patients and was infrequently the actual cause of death and so every effort needs to be made to bring down the mortality rates and hospital stay associated with anastomotic leak.