Introduction: Cholesteatoma is traditionally diagnosed by otoscopic examination and treated by surgery. Imaging in an uncomplicated case remains a controversy. This study was planned to correlate preoperative high-resolution computed tomography (HRCT) and intraoperative findings in patients with squamous chronic otitis media and to investigate the usefulness of a preoperative HRCT scan in depicting the status of middle ear structures in the presence of a cholesteatoma. Materials and methods: (a) To compare the preoperative HRCT temporal bone and surgical findings in patients with squamosal chronic otitis media; (b) To evaluate the role of HRCT temporal bone in the assessment of squamosal chronic otitis media. A prospective observational study was conducted between September 2015 and August 2017 in the Department of Otorhinolaryngology, Dr Ram Manohar Lohia Hospital and PGIMER, New Delhi. Total seventy diagnosed cases of squamous chronic otitis media were included, and their preoperative HRCT temporal bone findings and intraoperative findings were correlated. Results: The sensitivity, specificity, and positive and negative predictive values of HRCT were 73%, 97%, 80%, and 95% respectively, for determining the presence of lateral semicircular canal dehiscence 75%, 93%, 86%, and 88% respectively, for determining the presence of facial canal dehiscence; 84%, 71%, 87%, and 75% respectively, for determining the presence of scutal erosion; 91%,90%,62%,98% respectively for presence of tegmen erosion; 100%, 96%, 50%, and 100% respectively, for detecting the presence of dural plate defects. Conclusion: The decision for surgical intervention should not be entirely based on the radiological interpretation. The operating surgeon should be well prepared to encounter conditions which are not reported by the radiologist preoperatively and modify the operating strategy accordingly. The HRCT scan acts a good preoperative imaging modality for the otologist to predict disease and to explain the possible outcomes to the patient.