Conflicting reports and surgeon opinions have contributed to a long-standing debate regarding the merits of the intact canal wall versus canal wall down approach to cholesteatoma. The objective of this analysis was to identify and synthesize available data concerning rates of recidivism after the two primary types of cholesteatoma surgery. PubMed, Cochrane Collaboration, and Google Scholar searches were performed and articles filtered based on predetermined exclusion criteria. Individually reported rates of recurrent and residual disease were extracted and recorded. Meta-analysis demonstrated a relative risk of 2.87 with a confidence interval of 2.45–3.37, confirming a significantly increased incidence of postoperative cholesteatoma when using an intact canal wall approach rather than a canal wall down approach. Next, rates of recidivism following the typical two-stage intact canal wall operation were compared with a single-stage canal wall down operation and found to be similar. In conclusion, we advocate that greater consideration should be given to the canal wall down procedure in initial surgical management and identify the need for further exploration of rates of recidivism after staged or second-look procedures.