Although sleep has been linked to activities in various domains of life, one under-studied link is the relationship between unhealthy sleep practices and conduct problems among adolescents. The present study investigates the influence of adolescents’ unhealthy sleep practices-short sleep (e.g., less than 6 h a day), inconsistent sleep schedule (e.g., social jetlag), and sleep problems-on conduct problems (e.g., substance use, fighting, and skipping class). In addition, this study examines unhealthy sleep practices in relationship to adolescent emotional well-being, defiant attitudes, and academic performance, as well as these three domains as possible mediators of the longitudinal association between sleep practices and conduct problems. Three waves of the Taiwan Youth Project (n = 2,472) were used in this study. At the first time-point examined in this study, youth (51 % male) were aged 13–17 (M = 13.3). The results indicated that all three measures of unhealthy sleep practices were related to conduct problems, such that short sleep, greater social jetlag, and more serious sleep problems were concurrently associated with greater conduct problems. In addition, short sleep and sleep problems predicted conduct problems one year later. Furthermore, these three unhealthy sleep practices were differently related to poor academic performance, low levels of emotional well-being, and defiant attitudes, and some significant indirect effects on later conduct problems through these three attributes were found. Cultural differences and suggestions for prevention are discussed.