Cholesteatoma, a challenging otolaryngological condition, necessitates accurate diagnosis to prevent severe complications. This study evaluates the diagnostic performance of non-echoplanar diffusion-weighted magnetic resonance imaging (DW-MRI) in primary cholesteatoma and recurrent cases following mastoidectomy. For primary cholesteatoma, DW-MRI exhibited a sensitivity of 86.3%, specificity of 100%, with a p value <0.001. In recurrent cases, DW-MRI achieved 100% sensitivity and 100% specificity (p-value <0.001). These compelling results suggest the potential of DW-MRI to reduce unnecessary surgeries and enhance patient care. Nevertheless, standardization and further research are crucial to optimize its clinical utility. Non-echoplanar DW-MRI emerges as a promising diagnostic tool for cholesteatoma, with the potential to minimize the need for second-look surgeries.