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Grounded by academic undermatching theories, this study examined whether high school factors such as educational aspirations, academic experience, social networks, community involvement, and academic achievement influenced high school graduates’ enrollment to very selective colleges. HS GPA, high school course rigor, and one’s social network, namely parents and counselors, were found to be significant and meaningful predictors of enrollment in very selective colleges. The academic predictors of entrance to very selective colleges was operationalized to analyze high school graduates’ academic qualifications and college match with an emphasis on the differences among racial/ethnic groups. By sharing the knowledge with the leaders in a school district, efforts can be made for equal educational opportunity.