Objective: Following cholesteatoma surgery, effective long-term hearing preservation in children is difficult and is not typically expected. Hence, long-term data on hearing outcomes are lacking. The aim of this study was to analyze long-term hearing outcomes in children following cholesteatoma surgery. Methods: For this study, 49 ears in 47 children (≤16 years) with acquired cholesteatomas following atticotomy-limited mastoidectomy with cartilage reconstruction (inside-out approach) during 1986–2010 were included. Pre- and post-operative recidivism-free audiometric results were compared. Hearing success was defined as a post-operative air conduction (AC) threshold of ≤30 dB (serviceable hearing). Logistic regression analyses were used to evaluate potential prognostic factors that independently contributed to the prediction of hearing success. These factors included stapes condition, pre-operative AC threshold, ossicular chain integrity, disease severity, age, and gender. Results: The mean duration of follow-up was 14.2 years. The post-operative AC (33.55 ± 15.42 dB) and air-bone gap (17.88 ± 12.94 dB) were significantly improved compared with the pre-operative AC (42.90 ± 16.47 dB, p < 0.001) and air-bone gap (30.23 ± 13.68 dB, p < 0.001). The probability of hearing success following surgery (40.8%) was significantly higher than prior to surgery (24.5%, p = 0.008). Multivariate logistic regression analyses revealed a statistically significant correlation between hearing success and stapes integrity only (p = 0.005). Conclusions: This study provides important information on effective long-term hearing preservation over a mean follow-up of 14 years. In addition, stapes destruction is an independent negative prognostic determinant of achieving hearing success. The prediction model in this study provides otologists with useful pre-operative information to inform patients and parents on expected hearing outcomes and may be useful for post-operative observations.