Private and public investments in early childhood education have expanded significantly in recent years. Despite this heightened investment, we have little empirical evidence on whether children today enter school with different skills than they did in the late nineties. Using two large, nationally representative data sets, this article documents how students entering kindergarten in 2010 compare to those who entered in 1998 in terms of their teacher-reported math, literacy, and behavioral skills. Our results indicate that students in the more recent cohort entered kindergarten with stronger math and literacy skills. Results for behavioral outcomes were mixed. Increases in academic skills over this period were particularly pronounced among Black children. Implications for policy are discussed.