Objective Equivalent outcomes, such as procedural safety and audiometry, have been reported between endoscopic ear surgery (EES) and microscopic ear surgery (MES). This study aims to determine if EES leads to decreased postoperative pain when compared with MES. Data Sources PubMed, OVID MEDLINE, Scopus, Web of Science, and Cochrane Central from 2000 to 2020. Review Methods A systematic review in accordance with the PRISMA guidelines and standardized bias assessment was performed. Studies containing original data on postoperative pain following EES and MES were included. Results Fourteen studies fulfilled eligibility: 7 retrospective studies, 6 randomized controlled trials, and 1 case series. Studies included surgery for cholesteatoma (n = 3), tympanoplasty/myringoplasty (n = 6), and stapedotomy (n = 5), pooling data from 974 patients. Postoperative pain was quantitatively described through a variety of numeric pain scores. Meta-analysis was performed on 11 studies. Among the 7 studies utilizing the numeric rating scale or visual analog scale, postoperative pain in the EES cohort was significantly lower than that of the MES cohort (standardized mean difference = −1.45 [95% CI, −2.05 to −0.85], P < .001). Similarly, pain scores were lower in the EES cohort among the 4 studies utilizing the Three Grades Pain Scale (odds ratio = 0.2 [95% CI, 0.09-0.45], P < .001). Additional qualitative strengths identified in EES included significant improvements in visualization, operative time, postoperative complications, and decreased need for canalplasty. Quality assessment indicated low to moderate risk of bias for all studies. Conclusion Meta-analysis confirms that EES results in significantly less postoperative pain when compared with MES. This surgical approach should be considered in the armamentarium of otologic surgeons, allowing for improved outcomes.