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Although substantial work has examined the influence of adolescent pregnancy on mothers’ developmental outcomes, few studies have investigated the influence of adolescent mothers’ educational attainment on their children's achievement. This article examined the reading and math achievement trajectories of children born to adolescent and nonadolescent mothers with various levels of educational attainment. Results demonstrate that higher levels of maternal education predicted children's higher initial achievement at kindergarten and growth in achievement through eighth grade. The achievement of children with adolescent mothers, however, never reaches parity with the achievement of their peers with nonadolescent mothers. Race also predicted achievement differences. Black and Latino children of adolescent mothers were at greater risk for underachievement.