Despite the known deficits in sleep that occur during adolescence and the high prevalence of substance use behaviors among this group, relatively little research has explored how sleep and substance use may be causally related. The purpose of this study was to explore the longitudinal bi-directional relationships between sleep duration, sleep patterns and youth substance use behaviors. Participants included 704 mostly white (86.4%) youth, 51% female, with a baseline mean age of 14.7 years. Self-reported substance use behaviors included past month alcohol, cigarette, and marijuana use. Sleep measures included sleep duration on weekends and weekdays, total sleep, weekend oversleep, and weekend sleep delay. Cross-lagged structural equation models, accounting for clustering at the school level, were run to determine the longitudinal association between sleep and substance use adjusting for socio-demographic characteristics, pubertal status, body mass index z-score, and depressive symptoms. Cigarette use and weekend sleep were bi-directionally related as were marijuana use and total sleep. No other bi-directional associations were identified. However, alcohol use predicted shorter weekend oversleep and marijuana use predicted increased weekend sleep and weekend oversleep. Sleep patterns and duration also predicted adolescents' cigarette, alcohol, and marijuana use. Sleep, both patterns and duration, and substance use among youth are intertwined. Future research is needed to explore these bi-directional relationships, as well as other important contextual factors that may moderate these associations.