Abstract Background Understanding the relationship between adolescent pregnancy and adult education and employment outcomes is complicated due to the endogeneity of fertility behaviors and socio-economic functioning. Studies exploring adolescent pregnancy have often relied on limited data to measure adolescent pregnancy (i.e. birth during adolescence or self-reports) and lack access to objective measures of school performance during childhood. Methods We use rich administrative data from Manitoba, Canada, to assess women’s functioning during childhood (including pre-pregnancy academic performance), fertility behaviors during adolescence (live birth, abortion, pregnancy loss, or no history of pregnancy), and adult outcomes of high school completion and receipt of income assistance. This rich set of covariates allows calculating propensity score weights to help adjust for characteristics possibly predictive of adolescent pregnancy. We also explore which risk factors are associated with the study outcomes. Results We assessed a cohort of 65,732 women, of whom 93.5% had no teen pregnancy, 3.8% had a live birth, 2.6% had abortion, and