Objectives: This study examined the association between the frequency of high-caffeine beverage intake and dental cariesrelated pain symptoms among Korean adolescents, and assessed whether this association differed by school level. Methods: Data from 54,653 adolescents who participated in the 20th Korea Youth Risk Behavior Survey (2024) were analyzed. Participants were categorized as non-, low-frequency, and high-frequency consumers of high-caffeine beverages. Dental caries–related pain symptoms were assessed using self-reported oral symptom items. Complex sample logistic regression analyses were conducted to examine the association between intake frequency and pain symptoms after adjusting for sex, academic achievement, economic status, and frequency of tooth brushing. Trend analyses treated intake frequency as an ordinal variable, and the interaction by school level was tested. Results: Higher frequency of high-caffeine beverage intake was associated with a greater likelihood of dental caries–related pain symptoms in both middle and high school students. Compared to non-consumers, both low- and high-frequency consumers showed increased odds of experiencing pain symptoms. A significant increasing trend was observed with a higher intake frequency (p for trend<0.001). No significant interaction was observed between intake frequency and school level. Conclusions: Frequent consumption of high-caffeine beverages was associated with increased dental caries-related pain symptoms among Korean adolescents regardless of their school level.