The aim of the study was to describe ossicle resorption in chronic otitis with cholesteatoma and correlate it with clinical parameters such as age, contralateral ear condition, tympanic membrane aspect, cholesteatoma pathogenesis and extension, associated lesions and hearing threshold. Preoperative clinical data were collected for 140 patients with chronic otitis with cholesteatoma, whose ossicles were evaluated during surgery. 82% of patients showed ossicle resorption, with incus damage in 78% of cases. Multiple involvement was found in 45% of cases and the incus-stapes association was the most frequent. In 13 patients (11%) with ossicle damage, the ossicular chain was in continuity with a hearing threshold similar to patients without ossicular resorption. Ossicles were always damaged in congenital cholesteatoma and in case of associated lesions. Cholesteatoma extension was related to the incidence of ossicle resorption (p < 0.0001). Air and bone conduction worsened as the number of involved ossicles increased, while the air-bone gap remained stable. In conclusion, the origin and location of cholesteatoma are related to the site of ossicular damage, which is subsequent to the contact between bone and cholesteatoma. Pure-tone audiometry and air-bone gap do not reflect actual ossicular chain status. None of the other preoperative clinical parameters considered were reliable predictors of the condition of the ossicular chain.