INTRODUCTION: Intraperitoneal sepsis due to anastomotic leakage significantly affects the outcomes of intestinal surgery. The aim of this retrospective review is to examine retrospectively general and local factors involved in anastomotic leakage and their prognostic value. MATERIALS AND METHODS: Between April 1998 and April 2008, 367 patients underwent elective (217=59%) or emergency (150=41%) primary colonic resection for benignan (77=21%) or malignant (290=79%) disease in our department. We performed the following operations; 124 right colon resections with immediate anastomoses (primary resection), 65 (52.4%) of which were emergency and 59 (47.6%) elective procedures; 171 left colon resections, 73 (42.7%) of which were emergency and 98 (57.3%) elective procedures, and 72 primary rectal resections, 12 (16.7%) of which were emergency and 60 (83.3%) elective procedures. The considered variables were stapled or manual anastomoses, protective stomas and medical comorbidities. RESULTS: The perioperative mortality rate was 6.6% for emergency and 3.6% for elective procedures. The leak rate was 8.7% (32/367), 13.3% for emergency and 5.5% for elective procedures. Fistula was observed in 7/124 (5.6%) ileocolic, 13/171 (7.6%) colo-colic and 12/72 (16.6%) colo-rectal anastomoses, 8 of which were fashioned during emergency surgery. Twenty-one patients with anastomotic dehiscence were treated conservatively (3 underwent reoperation), while 11, with severe dehiscence, in all cases in the left colon, underwent an emergency Hartmann’s procedure, with a perioperative mortality rate of 35.7%. CONCLUSIONS: In our experience, the site of colonic anastomosis represents the risk factor most strictly related to the anastomotic leak rate, while other technical factors seem weakly associated with leakage. A significantly high percentage of patients (65.6%) with anastomotic fistulas have medical comorbidities.