Cholesteatoma is a benign tumor of the middle ear. Tympanoplasty is performed to remove cholesteatoma, prevent recurrence, and avoid complications. Previously, microscopy was used for tympanoplasty; however, endoscopy has become increasingly popular for this procedure. The effectiveness of endoscopy and the appropriate candidacy for endoscopic ear surgery remain controversial. In this retrospective chart review study, we enrolled 107 patients with cholesteatoma who underwent tympanoplasty and compared the microscopic approach (71 patients) and the endoscopic approach (36 patients) at different stages to clarify the benefits of using endoscopy and to determine candidacy for endoscopic ear surgery. Approach selection, complication rate, recurrence rate, and postoperative hearing threshold were compared between microscopic and endoscopic approaches in stages I, II, and III. Endoscopy was used more often than microscopy for early-stage (stage I) cholesteatoma (p = 0.005) and less frequently for advanced-stage (stage II) cholesteatoma (p = 0.02). Endoscopy surgery resulted in chorda tympani injury less often than microscopic surgery (p = 0.049); however, there were no significant differences between these two groups in terms of recurrence rate or postoperative hearing outcome. Endoscopy is particularly useful for early-stage cholesteatoma, and both approaches show no difference in hearing outcome in stage I and II; nevertheless, further research is required to determine an appropriate approach for more advanced stages (stage III).