Background/Objective: Anastomotic leakage (AL) is one of the most severe complications following colorectal cancer surgery and is associated with increased short and long term mortality. The literature is conflicting regarding increased risk of recurrence after AL. The aim of this study was to systematically review the impact of anastomotic leakage on the risk of local or distant recurrence and overall survival, cancer specific survival, and disease-free survival. Methods: A systematic review and meta-analysis was conducted in accordance with the PRISMA guidelines. A systematic search in PubMed, EMBASE, CINHAL, and The Cochrane Library was performed and meta-analyses were performed on all outcomes including analysis based on time-to-event data. Results: A total of eighteen cohort studies, including 69,047 patients whereof 2,555 patients had anastomotic leakage, were included. Meta-analysis demonstrated no significant effects of anastomotic leakage on local recurrence (RR 1.16, 95% CI 0.84–1.59) or distant recurrence (RR 1.44, 95% CI 0.52–3.96). Anastomotic leakage decreased overall survival (RR 0.85, 95% CI 0.77–0.94), disease free survival (RR 0.80, 95% CI 0.72–0.89), and cancer specific survival (RR 0.90, 95% CI 0.83–0.97). A time-to-event analysis was conducted on available data and the results were congruent with the frequency analyses. Conclusion: Anastomotic leakage following colonic resections is significantly associated with impaired overall survival, disease free survival and cancer specific survival. The study did not show any statistically significant association between anastomotic leakage and recurrence.