Cholesteatoma is often treated surgically using canal wall-preserving techniques. Clinical and otoscopic diagnosis of residual or recurrent disease after this form of surgery is unreliable and thus radiological imaging is often used prior to mandatory "second-look" surgery. Imaging needs to be able to differentiate residual or recurrent disease from granulation tissue, inflammatory tissue or fluid within the middle ear cavity and mastoid cavity. High-resolution computed tomography (HRCT), conventional magnetic resonance imaging (MRI), and delayed contrast MRI have all been used in detecting postoperative cholesteatoma. Although delayed contrast MRI performs better than HRCT and conventional MRI, the sensitivities and specificities of these different imaging methods are relatively poor. Diffusion-weighted MRI (DWI and, in particular, non-echo planar DWI) has been shown to have a high sensitivity and specificity for detecting recurrent cholesteatoma. In this review we provide examples of postoperative imaging appearances following cholesteatoma surgery and we review the relevant literature with an emphasis on studies evaluating the diagnostic accuracy of DWI.