This 1-year prospective study aimed to examine associations between children's preschool emotional and behavioral problems and their kindergarten classroom engagement, and to identify any gender differences in this association. In preschool, parents and teachers completed questionnaires assessing aspects of children's (n = 575) emotional and behavioral problems. Teachers rated children's engagement levels 1 year later in kindergarten. Compared with girls, boys showed higher levels of preschool hyperactivity/inattention and conduct problems, and lower kindergarten engagement. Regression analyses revealed that boys' higher hyperactivity/inattention levels almost completely accounted for their engagement disadvantage. However, the lack of interactions suggested that emotional/behavioral problems were related to engagement similarly for boys and girls. Preschool emotional and behavioral problems appear to be important correlates of kindergarten engagement and may be worthwhile targets for early intervention. Though girls and boys may benefit similarly from interventions, boys are disadvantaged from preschool onward and may benefit from greater support.