The current 5-year longitudinal study examined the effects of middle school bullying and victimization on adolescent academic achievement, disciplinary referrals, and school attendance through high school (N = 2030; 1016 both boys and girls). Greater engagement in bullying behaviors was concurrently associated with lower achievement and school attendance for girls and higher levels of disciplinary problems, and, for girls, predicted increases in disciplinary referrals through high school. Victimization was unrelated to school adjustment difficulties when controlling for bullying. Moreover, academic achievement was longitudinally associated with disciplinary referrals and school attendance. These findings outline concurrent school adjustment difficulties associated with engagement in bullying behavior, the longer-term behavioral ramifications for girls, and the relations of behavioral and academic development from middle school to high school.