Context: Deep infiltrating endometriosis (DIE) is a specific form of endometriosis in women, causing infertility and pelvic pain during reproductive age. Surgery is the treatment of choice for managing DIE, as medical therapy alone cannot adequately control symptoms. Objectives: The present study aims to investigate the recurrence and pregnancy rates following surgical treatment of DIE in women of reproductive age. Methods: PubMed, Web of Science, Scopus, Google Scholar, Cochrane Library, and ProQuest databases were searched from 2010 to August 25, 2024, using appropriate MeSH keywords. The quality of the included studies was assessed using the Mixed Method Appraisal Tool (MMAT), version 2018. Results: A total of 41 studies were included in the systematic review, and 34 studies were included in the meta-analysis. The meta-analysis comprised 6,585 individuals from 14 countries. The pooled estimated prevalence of endometriosis recurrence was 13% (95% CI: 11–17%, I²: 96.5%, Tau²: 0.01, Observations: 35). The corrected pooled estimated pregnancy rate after surgery for endometriosis was 47% (95% CI: 36–57%, I²: 96.47%, Tau²: 0.05). Conclusions: Recurrence and pregnancy rates remain controversial challenges in the surgical management of DIE. This study indicates a relatively low recurrence rate after DIE surgery and an improvement in the approximate pregnancy rate following the surgical approach.