Objectives: The objective of the study was to investigate the related factors of preventive behavior experience toward dental caries and periodontal disease in Korean adolescents. Methods: The study subjects were 72,060 adolescents in 800 schools who completed 2014 Korean Youth Risk Behavior Web-based survey. Dependent variables included general characteristics of the subjects, oral health behavior, and oral disease experience. The experience rate of sealant and scaling showed the prevention behavior of dental caries and periodontal disease. Data were analyzed by IBM SPSS statistics 20.0. Results: The experience rate of sealant accounted for 26.9%. The experience of sealant was related with gender, school, maternal education level, economic status, vigorous physical activity, smoking, usual stress, fruit consumption, milk consumption, soda consumption, snack consumption, tooth brushing, oral health education experience, periodontal bleeding and pain, mucosal disorders, and bad breath. The experience rate of scaling was 22.6%. The experience of scaling was related with gender, school, city division, learning achievement, maternal education level, economic status, residential type, vigorous physical activity, usual stress, fruit consumption, milk consumption, tooth brushing, oral health education experience, periodontal bleeding and pain, mucosal disorders, and bad breath. Conclusions: To expand preventive oral health behavior in the adolescents, it is necessary to support the systematic policy making and monetary establishment in the future.