Adolescents attending alternative high schools often present with high rates of academic and behavior problems. They are also at increased risk of poor health behaviors and engaging in physical violence compared with students in traditional high school settings. To address the needs of students in these educational settings, examining factors that influence academic problems in this population is essential. Research has established that both bullying/victimization and sleep problems increase adolescents’ risk for academic problems. Little is known about how these 2 factors together may exacerbate risk for academic problems among students attending an alternative high school. The current study investigated the interaction between teacher-reported bullying, victimization and daytime sleepiness on academic concerns (attention and learning problems) among a sample of 172 students (56% female; age M = 18.07 years, SD = 1.42) attending an alternative high school in a large, Southeastern U.S. city. Findings from path models indicated that daytime sleepiness, bullying, and victimization were uniquely associated with attention and learning problems. Further, significant interactions indicated that the association between victimization/bullying and attention/learning problems weakened as levels of daytime sleepiness increased. Results suggest the importance of assessing and addressing multiple contextual risk factors in adolescents attending alternative high schools to provide comprehensive intervention for students in these settings.