The trajectories of late preterm development from infancy to kindergarten reading and math, and predictors of academic resilience and risk are unknown. Sample included 1200 late preterm infants (LPIs) from the Early Childhood Longitudinal Study, Birth Cohort. Objective measurements of development at 9 and 24 months (Bayley-SFR) and reading and math academic achievement at preschool and kindergarten were standardized; trajectories of late preterm development from 9 months to kindergarten reading and math were identified using latent class growth analysis. Multinomial logistic regression [aOR, 95% CI] identified predictors of academic resilience and risk. Four trajectory groups were observed for reading and three for math. More optimal trajectories (in reading and math) and academic resilience were associated with experiencing sensitive parenting and preschool attendance. Suboptimal (at-risk) trajectories (in reading or math) and an increased odds of academic risk were associated with <high school education, twin/multiple gestation, prenatal smoking and male sex. LPI trajectories varied from infancy to kindergarten. More sensitive parenting and preschool attendance predicted academic resilience, and should be encouraged. Select risk factors (prenatal smoking, twin/multiple gestation, male sex, <high school education) predicted academic risk, and can help identify LPIs who might benefit from closer monitoring prior to school entry. Late preterm infants (LPIs) have developmental risks compared to full terms. LPI trajectories of early reading and math varied from infancy to kindergarten. We identified predictors of academic resilience and risk, which can help inform anticipatory guidance provided to LPIs prior to kindergarten. Promotive factors (sensitive parenting and preschool enrollment) predicted academic resilience. Select maternal and neonatal characteristics (<high school education, male sex, prenatal smoking, and multiple gestation) predicted academic risk at kindergarten. LPIs account for the majority of preterm infants. Encouraging preschool enrollment and fostering sensitive parenting may promote early academic achievement in LPIs, which has population-level impacts.