Considerable interest is directed to promoting children's success as they transition to kindergarten. It is generally proposed that children who experience lower levels of transition difficulties at kindergarten entry achieve higher academic and social-emotional gains, although this premise has seldom been explicitly evaluated in tandem with children's kindergarten readiness skills. To improve understanding of the consequences of transition difficulties, this study investigated the role of transition difficulties at the child level to children's achievements at the end of the kindergarten year in a Midwestern state in the US. Results from a series of covariate-adjusted regression models showed that children who experienced less transition difficulties at the beginning of kindergarten demonstrated relatively more gains in math, reading, and social-behavioral skills at the end of kindergarten, even when controlling for kindergarten readiness skills, child and family characteristics, and classroom-level contextual factors. The findings also indicated that the associations between kindergarten transition difficulties and academic and social-behavioral skill development at the end of kindergarten did not vary by children's academic and social-behavioral skills at kindergarten entry. Taken together, these findings suggest that transition difficulties that children encounter within the kindergarten context may have significant and independent implications for children's skill development. Possible practices to ease transition difficulties are discussed. [This paper was published in "Early Childhood Research Quarterly."]