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Despite a great amount of research on the topics of school-to-work transition, school mediated job-search systems, and high school vocational education and training (VET) in Japan, gender differences in job outcomes are a largely missing topic in the literature. Thus, this paper examines the interlocking effects of school mediated job-search systems and de facto gender segregation in VET on occupational attainments among Japanese women. Descriptive statistics find that women in female-dominant occupations are more likely to be employed in permanent positions and have higher occupational prestige scores. Logistic regression analysis finds that school mediated job-search systems, which include either or both of school referrals or the various supports provided by in-school job placement offices increase women’s likelihood to enter female-dominant occupations. Yet, women’s education levels and attendance at VET programs did not have a clear effect on the odds of being employed in female-dominant occupations. Discrete-time event history analysis finds that women who used school mediated job-search systems are more likely to experience first-entry job-turnover compared to those who did not, while this difference did not occur for men. The analysis finds no generational differences among women while in the case of men, younger cohorts are more likely to experience job-turnover compared to older cohorts. Overall, the findings of this paper suggest that there is persistent gender segregation in the Japanese labor market, which negates the effects of generational, class, and education differences on women’s job outcomes. Moreover, under the institutionally coordinated Japanese labor market, school mediated job-search systems, which are associated with school-employer linkages, reinforce these gendered hiring practices.