This study uses Trivers-Willard hypothesis to explain the differences in daughters’ and sons’ educational outcomes by parental background. According to the Trivers-Willard hypothesis (TWH), parental support and investments for sons and daughters display an asymmetrical relationship according to parental status because of the different reproductive advantage of the sexes. It predicts that high-status parents support sons more than daughters, and low-status parents support daughters more than sons. In modern societies, where education is the most important mediator of status, the TW hypothesis predicts that sons from high-status families will achieve higher educational outcomes than daughters. Using cohorts born between 1987 and 1997 from the reliable full population Finnish register data that contain the data of over 600.000 individuals, children’s educational outcomes were measured using data on school dropout rate, academic grade point average (GPA), and general secondary enrollment in their adolescence. OLS and sibling fixed-effect regression that permitted an examination of opposite-sex siblings’ educational outcomes within the same family were applied. Sons with high family income and parental education, compared to daughters of the same family, have lower probability of dropping out of school and are more likely to enroll into academic secondary school track. In families with low parental education or income daughters have lower probability for school dropout and enroll more likely to academic school track related to sons of the same family. The effect of family background by sex can be interpreted to support TWH in dropout and academic school track enrollment but not in GPA.