Introduction: Otitis media with effusion (OME) is a common middle ear condition, which frequently affects children and can lead to hearing impairment, speech delays, and developmental issues. Early childhood caries (ECC) is another prevalent pediatric condition defined by the presence of decayed, missing, or filled tooth surfaces in children under six years old. Objectives: This study aims to determine the prevalence of OME and ECC, the association between these two conditions, and the risk and severity of ECC among preschool children with OME. Methodology: A prospective cross-sectional study was conducted at a single tertiary center. A total of 206 preschool children aged six and below with hearing impairment or speech delay were recruited. They were grouped as follows: with OME (n= 129) and without OME (n = 77). Demographic and socioeconomic data were obtained, followed by otoscopy, anterior rhinoscopy, and tympanometric assessment. The subjects were further stratified into having ECC or not by conducting a dental examination for caries detection, whose findings were documented using Dental Charting and Caries Risk Assessment (CRA). Tympanometric width (TW) was also analyzed to measure its association with tympanic membrane appearance. Results: 51.5% (n=106) of children with OME were found to have ECC. They predominantly had mild ECC (49.1%), and most (51%) were at moderate risk for caries based on the CRA (P < 0.001). A significant association between OME and ECC was observed (p < 0.001). Tympanometry results documented a strong correlation between TW greater than 200 daPa and abnormal tympanic membrane findings in OME (P< 0.001). Conclusions: The association between OME and ECC in preschool children necessitates integrated healthcare approaches for early detection and management. Reliable diagnostic tools, such as tympanic width measurement for OME and CRA for ECC, are crucial in addressing these health issues. Early intervention and comprehensive care can mitigate the risks and improve health outcomes for affected children.