The increasing prevalence of sleep problem and its’ detrimental effects on adolescents’ development have received substantial attention. Sleep problems has been linked to academic problems, anxiety or depressive symptoms, overweight, and externalizing problems. It is essential to understand the antecedents and outcomes of adolescents’ sleep problems in order to identify targeted interventions. There is considerable evidence suggesting that social connectedness with peers is a powerful predictor of adolescents’ sleep health. Previous studies have documented the role of negative social connectedness with peers in adolescents’ sleep quality. Deviant peer affiliation is a core characteristic of negative social connectedness with peers. To our knowledge, few research has focused on the association between deviant peer affiliation and adolescents’ sleep problems. Moreover, its causal direction has not been determined. Thus, this study used a two-wave cross-lagged panel analysis to explore the likely causal direction between deviant peer affiliation and adolescents’ sleep problems. Participants were 887 adolescents (43.90% boys; Mage = 15.55) who provided self-report data on deviant peer affiliation and sleep quality as well as demographic variables at the beginning and the end of a school year. We used the questionnaire of deviant peer affiliation developed by our study team to assess deviant peer affiliation. In addition, Pittsburgh Sleep Quality Index (PSQI) was used to measure adolescents’ sleep problems. All the measures have good reliability and validity. We first calculated descriptive statistics for our variables of interest, followed by bivariate associations among these variables in SPSS 21.0 software, and the follow-up cross-lagged model was conducted using Mplus 7.0. After controlling for sex and age, we found that sleep problems at the beginning of the school year were a significant and positive predictor of deviant peer affiliation at the end of the school year (b2 = 0.12, SE = .05, p < .05), but deviant peer affiliation at the beginning of the school year did not predict sleep problems at the end of the school year (b1 = –0.07, SE = .06, p > .05). In summary, the current study is an important step towards a better understanding of the relation between deviant peer affiliation and adolescents’ sleep problems. It shows that higher level of sleep problems predicted more deviant peer affiliation over time, rather than the reversed direction. Attempts to decrease adolescents’ deviant peer affiliation should consider the importance of a good night’s sleep given the evidence that sleep problems can serve as a risk factor for deviant peer affiliation. These findings contribute to understanding the antecedents and outcomes of adolescents’ sleep problems and have important implications for interventions aimed at boosting adolescents’ positive development.