At the onset of puberty, students shift their sleep to later hours, but school starts early. It is suggested that evening orientation and early school start times do not go well together. Therefore, the aim of this study was to investigate sleep problems in adolescence, and it was expected that the adolescents’ eveningness orientation is associated with many sleep-related problems. Students of secondary education (n = 3201; mean = 13.8 ± 1.8 years) filled out a self-report questionnaire containing measures of morningness–eveningness, sleep time (midpoint of sleep, social “jetlag”), sleep length (on schooldays and on weekends), sleep quality, and sleep hygiene as well as questions on electronic screen media use. The impact of circadian preference on sleep time (midpoint of sleep and social jetlag), sleep length (on schooldays and on weekends), sleep quality, and sleep hygiene of adolescents was tested via multilevel analyses while controlling for covariates on the student level (age, sex, screen media use, and time leaving home) and on the class level (school type, grade level, and school start time). Morningness–eveningness was a significant predictor of all dependent variables and associations were highest (β > 0.40) for midpoint of sleep, social jetlag, problems in going to bed, problems in falling asleep, and problems in returning to wakefulness. Providing guidance for parents on sleep hygiene behavior routines for their child, an educational program in sleep hygiene, and later school start times could help to synchronize adolescents’ circadian rhythms to daily educational and social demands.