Previous research has established that higher levels of behavioral self-regulation are associated with higher levels of language and literacy. In this study, we take a more developmental perspective by considering how trajectories of self-regulation development (early, intermediate, late) predict the way literacy and language skills develop from preschool through second grade. Children (n = 351) were assessed twice per year for up to four years on indicators of decoding, reading comprehension, phonological awareness, and vocabulary. Using non-linear growth curve models, we found that children who demonstrated self-regulation earlier had higher language and literacy skills throughout preschool to second grade. More specifically, earlier self-regulation trajectories were associated with both higher levels and earlier development of both decoding and reading comprehension, but not faster development. Children with early self-regulation trajectories developed phonological awareness earlier than those with late self-regulation trajectories. Finally, children with early self-regulation trajectories had higher levels of vocabulary than children with intermediate trajectories, but did not differ on the rate or timing of vocabulary development. Findings point to the enduring and interconnected nature of self-regulation and children's language and literacy development.