Aims: Optimal treatment strategies for managing paediatric cholesteatomas remain controversial. This study aims to investigate the differences in clinical presentation, recurrence rates, and hearing outcomes in children with cholesteatoma. Methodology: A retrospective review of all paediatric cholesteatoma cases in a single surgeon centre over 15 years was performed. Data was collected on patient demographics, presentation, type and location of cholesteatoma, surgical approach, recurrence rates, and pre-and postoperative hearing outcomes. Results: A total of 59 patients underwent surgery for cholesteatoma or middle ear atelectasis during this period. The mean age of patients was 9.3 years and 61% were male. The most common surgery was the intact canal wall (ICW) technique, performed in 65% of cases. Other procedures included canal wall down (CWD), Atticotomy, Myringoplasty, and Tympanoplasty. Those undergoing CWD had worse hearing pre-operatively and post-operatively compared with children with the ICW approach. Although no statistical difference was noted, this trend is most likely a result of the tendency to perform ICW for less severe disease. Recurrence rates were dependent on timing and type of surgery: ICW showed 20% recurrence, CWD showed 28% recurrence and the Atticotomy group there was no recurrence. Conclusions: Management of paediatric cholesteatoma is a challenge, and demonstrates significant variability in presentation, recurrence rates, and hearing outcomes. Based on the literature and our surgical outcomes, the management of acquired cholesteatoma (AC) or middle ear atelectasis should be individualized for each patient. Recidivism is high in paediatric cholesteatoma, irresective of surgical approach, warranting long term follow up.