Objectives: We analyze the impact of adolescent motherhood on several education and labor market outcomes in Chile over the 1990–2013 period. We explore whether effects are different across income levels, timing of adolescent births, and three sub-periods. Methods: Using the CASEN national household survey, we applied propensity score-matching methods on two samples of women aged 24: one for women in the 2009–2013 period and another sample of 24-year-old women living with their mother between 1990–2013. Results: In both samples, adolescent motherhood has negative effects on educational outcomes (high school completion, enrollment in technical institutes and universities, and years of education) and on labor outcomes of non-poor women. Childbearing in early adolescence is associated with worse outcomes, and the adverse effects of adolescent motherhood on education and labor outcomes have diminished over the period. Conclusions: Similar to results in developed countries, adolescent motherhood has negative consequences on women’s education and labor outcomes, particularly on women that become mothers early in adolescence. Public policies aimed at reducing teen motherhood will have important effects on young women’s education and employment.