Cholesteatoma is a progressive and destructive middle ear disease that can lead to severe complications such as hearing loss, bone erosion, and even intracranial infections if left untreated. Accurate preoperative evaluation is crucial for the successful surgical management of this condition. High-Resolution Computed Tomography (HRCT) has become the gold standard in evaluation of extent of cholesteatoma due to its ability to reveal anatomical details of the middle ear. This study compares the accuracy of clinical and preoperative HRCT findings with intraoperative observations in patients with Cholesteatoma. Fifty patients diagnosed with Cholesteatoma who underwent surgical intervention were retrospectively analyzed. Patients aged 18 years and above diagnosed with acquired cholesteatoma. Who underwent HRCT imaging and Clinical Evaluation prior to surgery and with complete intraoperative findings documented during surgery were included in this study. Sensitivity, specificity, positive predictive value (PPV), and negative predictive value (NPV) were calculated to assess the diagnostic performance of clinical evaluation and HRCT against intraoperative findings. A total of 50 patients were included in our study, out of which 30 were males and 20 were females. Majority of patients were within the 31–40 years age group. In our study the comparison between HRCT findings and intraoperative observations, we found that incus erosion through computed tomography (CT) 40 cases was almost the same as during surgical observation in 39 cases. Malleus appeared eroded on CT in 33 cases however, 37 cases were seen with that observation during operation.The sensitivity, specificity, positive predictive value, and negative predictive value were 100% for detecting sigmoid plate erosion, dura exposure and malleus-incus joint discontinuity through preoperative CT. Our findings show that HRCT has superiority in assessing the involvement of vital structures compared to clinical evaluation, making it a mandatory tool for preoperative planning.