Background: Previous studies have shown that poor family environments are related to more sleep problems; however, little is known about how family irregularity in early life affects the development of sleep problems over childhood using objective sleep measures. The current study tests the hypothesis that early family irregularity contributes to the development of sleep problems. Methods: This population-based study comprises 5,443 children from the Generation R Study. Family irregularity was measured with seven maternal-reported questions on family routines when children were 2 and 4 years old. Mothers reported on sleep problems at child age 3, 6, and 10 years, whereas children completed questionnaires on sleep problems at age 10. Additionally, we used tri-axial wrist accelerometers for five nights in 851 children (mean age 11.7 years) to assess sleep objectively. Results: Family irregularity was associated with more mother- and child-reported sleep problems at ages 3, 6, and 10 years as well as with a shorter sleep duration and later objective sleep onset, but not with sleep efficiency or waking time. The association between family irregularity and multi-informant subjective sleep problems at age 10 years was mediated by mother-reported child psychopathology at age 6 years. Conclusions: Our findings show a long-term robust association of preschool family irregularity with more sleep problems during childhood as well as shorter sleep duration and later sleep onset as measured objectively with actigraphy. In part, these sleep problems were associated with family irregularity by way of child psychopathology. These findings suggest that interventions improving preschool family irregularity, which are targeted to reduce child psychopathology, may also impact the development of sleep problems beneficially.