Aim: To analyse diagnostic accuracy of MRI-DWI in detecting residual disease after cholesteatoma surgery and propose an optimum follow-up (FU) scheme. Method: A retrospective chart review of patients who had cholesteatoma surgery in a tertiary referral centre. 3T non-echo planar diffusion weighted imaging was performed as part of routine FU or indicated on the basis of clinical suspicion of disease. Imaging outcome was verified per-operatively during a second-look procedure or ossicular chain reconstruction. Diagnostic parameters were calculated and stratified by FU length. Results: For the FU of 664 cholesteatoma surgeries, 1208 MRI-DWI were obtained and 235 second-look procedures were performed. Most MRI-DWI were obtained within 1.5yrs of surgery. In this period, significantly less true positive MRI-DWI for residual disease and significantly more false negative MRI-DWI were found compared to other FU periods. Scanning after approximately 3yrs yielded a significantly higher rate of true positive MRI-DWI, while sensitivity surpassed 80%. Younger patients had a higher risk of developing residual disease. Patients undergoing canal wall up surgery, as well as patients <12yrs, were at risk for false negative MRI-DWI. Obliteration reduces the risk of residual disease, while leading to less false negative MRI-DWI. Conclusion: Based on our findings, a novel radiologic FU scheme for detecting residual disease is suggested for stable ears after cholesteatoma surgery: standard MRI-DWI approximately 3 and 5yrs after primary surgery, as well as MRI-DWI after approximately 9yrs for patients with specific risk factors (i.e. patients <12yrs or patients undergoing canal wall up surgery without obliteration).