Background: Anastomotic leakage is the most serious surgical complication following colorectal resection, and surgical intervention is often required. The purpose of the study was to investigate short- and long-term outcomes after reoperation for anastomotic leakage. Method: Patients with a symptomatic anastomotic leakage following a laparoscopic colorectal cancer resection from January 2009 to December 2014 were identified from our local prospective database. Patients were grouped according to the management of anastomotic leaks: local, lap, or open approach. Primary outcomes were length of stay, chance of bowel continuity, and overall mortality. Results: A total of 113 patients were included. The median follow-up time was 40 months (0–82 months). Overall mortality was significantly associated with UICC stage III–VI disease (vs. UICC stage I–II disease) [adj. HR 5.35 (CI 2.32–12.4), p = 0.0001] and minimal invasive reoperation compared with open approach [local: adj. HR 0.12 (CI 0.03–0.52), p = 0.004; lap: adj. HR 0.32 (CI 0.12–0.86), p = 0.024]. Chance of bowel continuity was significantly increased in younger patients below 67 years [adj. OR 6.15 (1.76–21.5), p = 0.004] and following a local procedure [adj. OR 7.45 (1.07–51.8), p = 0.043]. Patients in the open group had significantly longer length of stay and time to initiation of adjuvant chemotherapy compared with those in the lap group. Conclusion: Our data confirms that minimal invasive reoperation for anastomotic leakage is a safe and feasible approach associated with short- and long-term advantages and can be chosen in selected cases.