OBJECTIVES: To compare the outcomes of endoscopic versus microscopic tympanoplasty during the initial period of a surgeon adopting the new endoscopic technique and teaching the surgical approach to residents assisting in surgery. METHODS: Retrospective medical chart review of 60 consecutive operations for repair of isolated tympanic membrane perforations from 2011 to 2016 performed by a single surgeon assisted by residents in an academic teaching hospital. The outcomes of 20 ears repaired microscopically before the senior author adopted endoscopic ear surgery (Group A) were compared with the outcomes of the first 20 ears that were attempted with endoscopic surgery (Group B) and the next 20 ears performed endoscopically (Group C). Sixty ear operations were performed on 52 patients as 8 patients had bilateral ear surgery. RESULTS: The tympanic membrane closure rate was 80% for Group A, 80% for Group B, and 95% for Group C. Mean air-bone gap improvement was 12.8 dB in Group A, 8.3 dB in Group B, and 12.1 dB in Group C. Mean duration of surgery was 99.2 minutes in Group A, 91.3 minutes in Group B, and 90.5 minutes in Group C. In Group B, 20% of the ears (4/20) were converted to a microscopic approach; in Group C, none required conversion. CONCLUSIONS: Maintenance of good outcomes and similar results can be maintained during a surgeon's transition to adopting endoscopic tympanoplasty and teaching it to residents.