Background: Cholesteatoma is a lesion capable of destroying surrounding tissues, which may result in significant complications. Surgical resection is the only effective treatment; however, the presence of cholesteatoma recidivism is common. This study evaluated the effectiveness of the Attic Exposure-Antrum Exclusion (AE-AE) surgical technique in treating cholesteatomas and identifying factors associated with recidivism. Additionally, the study aimed to assess the utility of non-echo-planar diffusion MRI (non-EPI-DWI MRI) in detecting cholesteatoma recidivism in patients undergoing AE-AE surgery. Methods: The study involved 63 patients who underwent AE-AE surgery for primary acquired cholesteatoma and were followed up clinically and radiologically for at least five years. The radiological follow-up included a non-EPI-DWI MRI. Results: Results showed that the AE-AE technique successfully treated cholesteatomas, with a recidivism rate of 5.2%. The study also found that non-EPI-DWI MRI was a useful diagnostic tool for detecting cholesteatoma recidivism, although false positives could occur due to the technique’s high sensitivity. As Preoperative Pure-tone average (PTA) increases, there is a higher probability of cholesteatoma recidivism in imaging tests (p = 0.003). Conclusions: Overall, the study highlights the importance of the AE-AE surgical technique and non-EPI-DWI MRI in managing cholesteatoma recidivism in patients, providing valuable insights into associated risk factors and how to manage recidivism. Non-EPI-DWI MRI can assist in patient selection for revision surgery, reducing unnecessary interventions and associated risks while improving treatment outcomes and patient care.