While access to higher education has reached gender parity in Taiwan, the phenomenon of gender segregation and stratification by fields of study and by division of labor persist. In this article, we trace the historical evolution of Taiwan's education system and data using large-scale educational databases to analyze the association of institutional factors and educational outcomes. Grouping in the college entrance examinations in the 1950s led to grouping in the high school curriculum, which, in turn, seems to have enlarged the mathematics performance gap between the natural sciences group and the social studies group, and extended to a performance gap between the two groups on the college entrance examination. Because men concentrate in science and engineering and women concentrate in humanities, the superiority of the former disciplines over the latter was consolidated along with the stereotype that male fields were better than female fields.