Background: Free and pedicled flaps are both valuable surgical strategies for lower limb reconstruction. Evidence that compares both techniques is scarce. Our aim is to synthetise all the comparative studies by conducting a meta-analysis to identify post-operative outcomes. Method: A systematic review of pubmed, EMBASE, Cochrane library, and Web of Science was conducted, aiming at articles comparing the outcomes of free versus pedicled flaps in lower limb reconstruction. A pooled analysis with the Mantel and Haenszel methods and random effect analysis provided results as a risk ratio with a 95% confidence interval. Results: 10 retrospective studies were selected. While the flap necrosis rate did not differ significantly between techniques (RR 1.35, 95%CI 0.76–2.39, p = 0.31), the partial flap necrosis rate was significantly lower in free flaps (RR 0.45, 95%CI 0.22–0.91, p = 0.03). The overall complication rate (RR 0.83, 95%CI 0.64–1.07, p = 0.16) and revision surgery rate (RR 1.38, 95%CI 0.55–3.50, p = 0.49) did not differ significantly. No significant difference was found in the high aesthetic satisfaction rate (RR 1.76, 95%CI 0.57–5.41, p = 0.32) and post-operative infection rate (RR 0.85, 95%CI 0.55–1.33, p = 0.48). Conclusion: Despite important variability in the choice of flaps and outcomes reported among studies, free and pedicled flaps appear to be reliable surgical strategies for lower limb reconstruction with similar surgical outcomes.