Purpose: To investigate the association between sleep duration, sleep initiation difficulties and psychological and somatic complaints. Methods: We used three cohorts of cross-sectional Swedish questionnaire data, from the Health Behaviours of School aged Children (1985/1986, 2005/2006, 2013/2014, n=>18 000, aged 11–15). Specific complaints (e.g. pain) and total complaint load were used as outcomes of sleep duration, sleep initiation difficulties and the combination of them both. Results: Sleeping less than recommended and sleep initiation difficulties were associated with increased odds of specific complaints and belonging to the group with the greatest complaint load. The combination of short sleep duration and sleep initiation difficulties were associated with higher odds than either sleep issue alone. No interaction effects between time and sleep variables were found regarding complaints. Conclusions: The findings support recent sleep duration recommendations. Further, sleep issues warrant a broad health assessment as they indicate a high likelihood of other complaints.