Aim: To evaluate the contralateral ear of patients with chronic otitis media (COM) and compare the pathology of the operated ear with the condition of the opposite ear. Material and Method: Patients with COM who had undergone tympanoplasty, tympanomastoidectomy, or radical mastoidectomy were analyzed retrospectively. The operated ears were evaluated for preoperative diagnoses, surgery types, the number of surgeries, intraoperative findings (middle ear mucosal conditions, presence of cholesteatoma, ossicular destructions, facial canal dehiscence, lateral semicircular, and dural defects), and postoperative ear conditions. The contralateral ear was classified as intact, or as presence of perforation, retraction, adhesion, and cavity. Results: In total, 523 patients with a mean age of 31.87 +/- 14.75 years were included in the study. Perforation (30.6%) was the most frequently detected pathology in the contralateral ear. There was no statistically significant association between the number of surgeries, presence of ossicular destruction, facial canal dehiscence, lateral semicircular defect, and dural defect, and contralateral ear condition (p > 0.05). However, there was a significant association between preoperative diagnosis, type of surgery, middle ear mucosal condition, presence of cholesteatoma, and postoperative condition, and contralateral ear condition (p < 0.05). Discussion: The perioperative condition of the middle ear should be acknowledged as a risk factor for surgical success in the presence of any abnormalities in the contralateral ear.