Objective: The study was designed to investigate the effect of extreme prematurity on growth in academic achievement across the early school years and the validity of kindergarten neuropsychological skills as predictors of achievement. Method: A 2001–2003 birth cohort of 145 extremely preterm/extremely low birth weight (EPT/ELBW) children from a single medical center, along with 111 normal birth weight (NBW) classmate controls, were recruited during their first year in kindergarten and followed annually across the next 2 years in school. Mixed model analysis was conducted to compare the groups on growth in achievement across years and examine kindergarten neuropsychological skills as predictors of growth. Results: The EPT/ELBW group scored significantly below NBW controls on all achievement tests across years and had higher rates of special education placement and grade repetition. Despite limited catch-up of the EPT/ELBW group to the NBW controls in spelling, group differences were generally stable. Differences in spelling and mathematics achievement remained significant when controlling for global intelligence or excluding children who had intellectual or neurosensory impairments or repeated a grade. Higher scores on kindergarten tests of multiple neuropsychological ability domains predicted higher achievement levels and steeper growth in achievement. Conclusions: The findings document persistent academic weaknesses in EPT/ELBW children across the early school years. Results point to the need for preschool interventions to enhance academic readiness and suggest that neuropsychological skills assessed in kindergarten are useful in identifying individual differences in early learning progress.