Background: Determine potential triggers for ovarian endometriosis recurrence to provide individualized long-term management and follow-up for improved patient outcomes. Methods: Relevant data were acquired through systematic retrieval from PubMed, Embase, Web of Science, and Cochrane Library before October 2022. We determined the odd ratio or the mean difference with their corresponding 95% confidence interval (CI) to explore the relationship between relevant risk factors and postoperative endometriosis relapse. Results: This meta-analysis ultimately covered 6388 patients from 18 trials, and the findings demonstrated that postoperative endometriosis recurrence was associated with the age at surgery [mean difference (MD) (95% CI) = –0.69 (–1.33~–0.05), p = 0.04], family history [odds ratio (OR) (95% CI) = 2.18 (1.10~4.29), p = 0.02], preoperative carbohydrate antigen (CA-125) [MD (95% CI) = 24.08 (–7.55~40.61), p = 0.004], laterality of endometriosis (EMs) [OR (95% CI) = 1.19 (1.00~1.40), p = 0.04], presence of adenomyosis [OR (95% CI) = 1.53 (1.11~2.11), p = 0.009], presence of myoma [OR (95% CI) = 1.44 (1.07~1.94), p = 0.02], previous endometriosis-related surgery [OR (95% CI) = 1.90 (1.45~2.51), p 0.00001], and r-American Fertility Society (r-AFS) stage [OR (95% CI) = 0.30 (0.19~0.46), p 0.00001]/[OR (95% CI) = 0.57 (0.48~0.66), p 0.00001]. In addition, postoperative pregnancy [OR (95% CI) = 0.40 (0.19~0.82), p = 0.01] and postoperative medication [OR (95% CI) = 1.64 (1.02~2.62), p = 0.04] were indicated protective factors for the prevention of postoperative ovarian endometriosis relapse. Conclusions: Risk factors for postoperative endometriosis recurrence included the age at surgery, family history, CA-125, laterality of EMs, presence of adenomyosis, presence of myoma, previous endometriosis-related surgery, and r-AFS stage. In addition, protective factors for preventing postoperative recurrence included postoperative pregnancy and postoperative medication. However, the age of menarche, infertility, the extent of surgery, cyst size, body mass index, and dysmenorrhea were unrelated to postoperative recurrence. The sample size could be increased for further investigations.