Abstract The present study examined the influence of schooling during children's first and second years of preschool for children who experienced different amounts of preschool (i.e., one or two years), but who were essentially the same chronological age. Children (n=76) were tested in the fall and spring of the school year using measures of self-regulation, decoding, letter knowledge, and vocabulary. Using hierarchical linear modeling (HLM), preschool was not associated with children's development of self-regulation in either year. For decoding and letter knowledge, children finishing their second year of preschool had higher scores, although both groups of children grew similarly during the school year. Thus, our results suggest that the first and second years of preschool are both systematically associated with decoding and letter knowledge gains, and the effects are cumulative (two years predicted greater gains overall than did one year of preschool). Finally, children's chronological age, and not whether they experienced one versus two years of preschool, predicted children's vocabulary and self-regulation outcomes. Implications for preschool curricula and instruction are discussed, including the increasing emphasis on literacy learning prior to kindergarten entry and the need to address self-regulation development along with academic learning.