The purpose of this study was to assess the impact of extreme prematurity on three global measures of school outcomes. Using a matched cohort design, exposed infants comprised all surviving singleton infants leqslant R: less-than-or-eq, slant 28 weeks gestation born at one regional neonatal intensive care hospital between 1983 and 1986 (n = 132). Unexposed infants comprised randomly selected full-term infants (geqslant R: gt-or-equal, slanted 37 weeks gestation) frequency matched on date of birth, zip code and health insurance. All children were selected from a regional tertiary children’s centre serving western New York population. Standardised telephone interviews elicited information on grade repetition, special education placement and use of school-based services. Unconditional logistic regression was used to estimate odds ratios (OR) and corresponding 95% confidence intervals (CI) adjusted for potential confounders for children without major handicaps. Extreme prematurity was associated with a significant increase in risk of grade repetition (OR = 3.22; 95% CI = 1.63, 6.34), special education placement (OR = 3.16; 95% CI = 1.14, 8.76) and use of school-based services (OR = 4.56; 95% CI = 1.82, 11.42) in comparison with children born at term, even after controlling for age, race, maternal education, foster care placement and the matching factors. These findings suggest that survivors of extreme prematurity remain at risk of educational underachievement.