Hypothesis: There is a difference in clinical characteristics, type of surgery and outcome between pediatric and adult cholesteatoma. Background: Pediatric cholesteatoma is a chronic disease with many challenges concerning diagnosis and treatment. There are no universally accepted opinions among otologists about the course, consequences and outcome of surgery for cholesteatoma in pediatric patients. There is also a difference in opinion concerning the choice of surgical technique. Methods: The patients were divided in three groups: children younger than 9 years (17), adolescents—10 to 16 years (25), and adults (265 cases). For all the children, closed tympanoplasty was performed, and reoperation or conversion to open tympanoplasty was done later if needed. Results: Post-operative audiometry had good audiological results, comparable to cholesteatoma surgery in adults. An air–bone gap up to 20 dB was achieved in 60% of children under 9 years, in 65% of children aged between 10 and 16, and in 65% of adults. During a post-operative course, retraction of neomembrane was found in 30% of younger children, 29% of adolescents, and in 9% of adults. Also, residual and recurrent cholesteatoma were more than twice as frequent in children. Reoperation was performed in 40% of children younger than 9, in 28% of children aged 10 to 16, and in 13% of adults. In half the cases of pediatric cholesteatoma reoperations, conversion to open tympanoplasty was done because of extensive disease. Conclusion: Adequate preoperative medicamentous and local treatment of cases with pediatric cholesteatoma are needed because of different sensitivity of bacteria and potential ototoxicity of antibiotics. Post-operatively functional and audiological results are comparable to adults, but during further follow-up, retraction pockets (30%) and recurrent cholesteatoma (20%) are found. Reoperation was performed in 32% children and conversion to open tympanoplasty in 25% of pediatric cholesteatoma cases. The age of the patient is a very important factor that determines the type of surgical procedure and the results of surgery for middle ear cholesteatoma.