Through multilevel analyses of Educational Longitudinal Study and National Center for Education Statistics (NCES)-Barron's data sets, this study examined unequal chances for college enrollment for students from different high school types and locations. The study shows that students from more privileged high school sectors are able to maximize attendance at better academically matched colleges and that the structural type and location of high school both as hierarchically ranked and as providing varied opportunities and norms are key factors in college matching. The problem of undermatching is more prevalent among students in urban public open schools, suburban disadvantaged public schools, and rural schools. In contrast, students in urban magnet test-in schools, suburban advantaged public schools, Catholic schools, and independent private schools exhibit markedly better patterns of college matching. Our findings reveal nuanced differences within each location and sector, and we explore mechanisms by which the diverse opportunity structure and culture of such varied high schools produce different college-matching results.