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This paper explores the role of family trajectories during childhood in explaining inequalities by maternal education in children's math and reading skills using harmonized, longitudinal, and nationally representative surveys, which follow children over the course of primary and lower secondary school in four high‐income countries (England, France, Germany, and the United States). As single parenthood and family transitions are more likely among less educated parents and are associated with fewer resources for children, we explore whether growing up outside a stable two‐parent family mediates educational inequalities in math and reading scores. Results show a strong educational gradient in family trajectories in the four countries, but this varies by child age and by country. Children who experience a family transition record lower test scores, although the magnitude differs by the type of postseparation arrangements. Overall, family trajectories are strongly associated with children's math and reading scores but, because of the importance of selectivity in family trajectories, they play only a modest role in explaining the skills gaps by maternal education, considerably less than determinants such as income. The penalties associated with not living within a stable two‐parent family are always larger in the United States and England than in France and Germany. [ABSTRACT FROM AUTHOR]