The potential for drug-drug interactions (DDIs) in dental care is a growing concern, especially for patients managing multiple medications or chronic conditions. However, detailed real-world data on the frequency and clinical significance of DDIs in dental practice remain limited. The aim of this study was to quantify the occurrence, seriousness, and clinical importance of DDIs in dental patients, and to examine how age and existing comorbidities influence DDI risk. A retrospective analysis was performed on 105 adult dental patients, examining demographic characteristics, preexisting health conditions, dental treatments, and medication records. DDIs were identified using the DrugBank Drug Interaction Checker, which categorizes interactions as major, moderate, or minor. Among the patients, 45.7% had one or more preexisting medical conditions, with cardiovascular disorders being the most frequent (19.0%). Dental diagnoses most commonly involved apical lesions (47.6%), and extractions were the leading procedure (53.3%), indicating substantial exposure to pharmacologic therapy. Of 1,332 possible drug pairs, 542 interactions were detected: 2.3% classified as major, 25.0% as moderate, 13.4% as minor, and 59.3% showing no interaction. Notable high-risk DDIs included combinations of epinephrine with beta-blockers. Age-stratified analysis revealed that patients aged 31–60 years experienced 61.3% of major DDIs, while those ≥61 years accounted for 38.7%; no major interactions were identified in the 0–30 years group. The elevated DDI incidence in the 31–60 cohort may reflect more accurate reporting of their medications. This study provides valuable real-world insights into DDIs within dental settings, highlighting the importance of thorough medication review, systematic screening for interactions, and targeted strategies based on patient age and comorbidities to optimize safety.