The purpose of this study was to examine the relationship between middle school students' college-going self-efficacy and their race, college generational status, academic self-concept, and perceived college-going culture. The respondents were 162 seventh and eighth grade students attending one middle school in southeastern United States who responded to four instruments that assessed the different variables. The researcher used a four-step hierarchical multiple regression analysis to determine the amount of variance accounted for by each of the predictor variables while controlling for the previously entered variables. In the final model, college generational status, academic self-concept, and college-going culture as a model accounted for 36% of the variance in middle school students' college-going self-efficacy. Although initially significant in the first two steps of the regression, race was not ultimately a significant predictor. This finding is possibly because it was significantly correlated with college generational status and academic self-concept. The findings suggest that as early as middle school there are student characteristics and contextual factors, namely race, college generational status, academic self-concept, and perceived college-going culture that contribute to students' confidence in their ability to attend college. This research is instrumental in understanding and addressing the achievement and opportunity gaps that are often evident among diverse student populations.