This preliminary investigation explored associations between African American students' perceptions of racial fairness, dimensions of school engagement (behavioral, emotional, cognitive) and school discipline (office discipline referrals, out-of-school suspensions), and the role of gender as an important social context for these associations. In this cross-sectional investigation, participants were 151 (78 girls; 73 boys) high school students from the southeastern United States who reported on their perceptions of the school's racial fairness and their engagement. Discipline outcomes were retrieved from school record data. For girls, results revealed a significant indirect relationship (small to medium effect) between perceived racial fairness and office discipline referrals through emotional engagement. For boys, a significant indirect association of perceived racial fairness on office discipline referrals (medium effect) and out-of-school suspensions (large effect) through behavioral engagement was found. Implications for our findings are discussed for the work of school psychologists.