Background: To evaluate the morbidity frequency measures in terms of the cumulative incidence of sympathetic ophthalmia (SO) triggered by single or multiple vitreoretinal (VR) surgery procedures in eyes without an antecedent history of trauma and previous ocular surgery, except for previous or concomitant uneventful lens extraction, and to further investigate the relationship between VR surgery and SO. Methods: A literature search was conducted using PubMed, Embase, and Scopus from inception until 11 November 2022. The Joanna Briggs Institute (JBI) critical appraisal checklist for the case series and the Newcastle–Ottawa Scale were used to assess the risk of bias. The research was registered with the PROSPERO database (identifier, CRD42023397792). Meta-analyses were conducted using the measurement of risk and a 95% confidence interval (CI) for each study. Results: A random-effect meta-analysis demonstrated that the pooled cumulative incidence of SO triggered by single or multiple VR surgery procedures in eyes without an antecedent history of trauma and previous ocular surgery, except for previous or concomitant uneventful lens extraction among patients who developed SO regardless of the main trigger, was equal to 0.14 with a CI between 0.08 and 0.21 (I2 = 78.25, z: 7.24, p < 0.01). The pooled cumulative incidence of SO triggered by single or multiple VR surgery procedures in eyes without an antecedent history of trauma and previous ocular surgery, except for previous or concomitant uneventful lens extraction among patients who underwent VR surgery, was equal to 0.03 for every 100 people, with a confidence interval (CI) between 0.02% and 0.004% (I2 = 27.77, z: 9.11, p = 0.25). Conclusions: Despite postsurgical SO being a rare entity, it is a sight-threatening disease. VR surgery should be viewed as a possible inciting event for SO and considered when counseling patients undergoing VR surgery.