Objective To investigate the prevalence of adolescent sleep disturbances and their relation with psychosocial difficulties and health risk behaviours we analysed data of a province-wide health survey (n=16,781). Methods Psychosocial difficulties were measured with the Strength and Difficulties Questionnaire. Additional assessments included self-reported sleep disturbances, suicidality and health risk behaviours including current use of tobacco, alcohol and drugs, physical inactivity and compulsive use of multimedia. We used multi-level analyses to investigate the relations including differences between boys and girls, as well as the mediating role of emotional problems. Results Just under 20 % of adolescents reported sleep disturbances in the previous month. These sleep disturbances were associated with psychosocial problems (OR: 6.42, p<0.001), suicidality (OR: 3.90 - 4.14, p<0.001) and all health risk behaviours (OR: 1.62-2.66, p<0.001) but not with physical inactivity. We found moderation by gender for the relations between sleep and suicide attempts (OR: 0.38, p<0.002) and sleep and cannabis use (OR: 0.52, p=0.002), indicating attenuated relations in girls compared to boys. Emotional problems partially mediated the relations between sleep disturbances and multimedia use. Conclusions The current study reiterates the high prevalence of sleep disturbances during adolescence. These sleep disturbances were strongly related to psychosocial problems and a wide range of health risk behaviours. Although the direction of causality cannot be inferred, the current study emphasizes the need for awareness of impaired sleep in adolescents. Moreover, the gender differences in associated suicide attempts and cannabis use call for further research into tailored intervention strategies.