Background As the aeration and drainage entrances in both ears are the same, the factors that produce otitis media in one ear may also affect the other. Also, the unsolved debate is that long-standing otitis media turns into chronic otitis media (COM). Hence, this study was conducted with the objective of assessing the incidence of abnormal findings in the contralateral ear (CLE) and to find the association between the type of COM of diseased ear with the findings of CLE. Materials and Methods A hospital-based cross-sectional study was conducted among cases with unilateral COM who visited the outpatient department of otorhinolaryngology at Chettinad Hospital and Research Institute in Chennai between November 2021 and February 2022. The study comprised 200 COM cases in all. The medical history, otoscopic examination, pure-tone audiometry, and tympanometric findings of the patient were all documented. SPSS version 20 was used to conduct the analysis. Results About 80% of the individuals with COM in one ear exhibited some abnormalities in the CLE. The type of COM in the afflicted ear is not linked with the otoscopic findings, type of hearing loss, tympanometric findings, or overall abnormalities in the CLE. This study's findings are comparable to those of several others. Conclusion Though there is no association between type of COM and the pathological findings in the CLE, considering the huge burden of pathological findings noted in the CLE, all cases of unilateral COM should be screened for aberrant findings in the CLE.