A retrospective analysis of the results of surgical treatment of 436 patients (332 adults and 104 children under the age of 15 years) with acquired middle ear cholesteatoma was performed to identify possible predictors of relapse of the process and a prospective assessment of the results of surgical treatment. It was revealed that the leading factors in the development of residual pathology were: the presence of cholesteatoma in the area of destruction of the bone wall of the canal of the facial nerve, cholesteatoma of the hypothympanum, cholesteatoma in the place of destruction of the bone wall of the posterior cranial fossa. The key reasons for the formation of recurrent pathology were: children under 15 years of age, closed surgery, pathological changes in the tympanic orifice of the auditory tube and the presence of cholesteatoma in its lumen. Performing a closed operation in adults with pathology of the tympanic orifice of the auditory tube increases the risk of recurrent cholesteatoma by 18.6%, and in children by 20%. The choice of a closed method of surgical intervention for the epitympanic type of the disease can increase the risk of residual pathology by 17.2% in adults and 27.8% in children.