Background and Objectives: In the presence of a persistent endodontic lesion or endodontic failure, the alternative for the recovery of the dental element is endodontic retreatment or endodontic surgery, which consists in the surgical removal of the root apices with retrograde closure of the endodontium. The objective of this systematic review and meta-analysis was to provide an updated value of the Risk Ratio between the two types of treatment in order to offer to clinicians who propose a non-surgical endodontic retreatment or an endodontic surgery a direct comparison. Materials and Methods: The revision was performed according to PRISMA indications: three databases (PubMed, Scopus and Cochrane register) were consulted through the use of keywords relevant to the revision topic: surgical endodontic retreatment, endodontic retreatment, apicoectomy. This search produced 7568 records which, after eliminating duplicates and applying the inclusion and exclusion criteria, resulted in a total of seven included articles. The meta-analyses were conducted by applying fixed-effects models, given the low percentage of heterogeneity. In addition, trial sequency analysis (TSA) was performed for the analysis of the statistical power of the results and GRADE for the quality of the evidence. Results: The results of the meta-analyses’ data report an aggregate risk ratio (RR) between non-surgical endodontic retreatment and surgical endodontic retreatment of: 1.05 [0.74, 1.47] at one year of follow-up; RR 2.22 [1.45, 3.41] at two years of follow-up; an RR 1.08 [0.73 1.62] for a follow-up period of 3–4 years; and an RR 0.92 [0.53, 1.61] for a follow-up period of 8–10 years. Conclusions: The results of the present meta-analysis show that in the long term, the risk of failure is identical for the two groups, and there is only a slightly higher risk of failure for non-surgical endodontic retreatments, when only two years of follow-up are considered.