This prospective cohort study investigated whether leisure boredom predicts high school dropout. Leisure boredom is the perception that leisure experiences do not satisfy the need for optimal arousal. Participants completed a self-report questionnaire which included the Leisure Boredom Scale. The original cohort of grade 8 students (n=303) was followed up twice at 2-yearly intervals. Of the 281 students at the second follow-up, 149 (53.0%) students had dropped out of school. The effect of leisure boredom on dropout was investigated using logistic regression taking into account the clustering effect of the schools in the sampling strategy, and adjusting for age, gender and racially classified social group. Leisure boredom was a significant predictor of dropout (OR=1.08; 95% CI: 1.01-1.15) in students 14 years and older, but not so in younger students (OR=1.0; 95% CI: 0.95-1.05). The study has shown that measuring leisure boredom in grade 8 students can help identify students who are more likely to dropout of school. Further research is needed to investigate the longitudinal association between leisure boredom and school dropout.