Multiply disadvantaged youths exhibit worse health and academic success than their less disadvantaged peers, possibly due to greater exposure to social status-based discrimination. Models that capture the additive burden of disadvantage in tandem with multiple forms of discrimination are needed to explicate the unique and combined impact of these factors on adolescent health and academic outcomes. In addition, protective factors like positive family and peer relationships may attenuate these relationships. This study used data from the Beyond High School Study (N = 9,658), which looked at the transition to adulthood among senior class cohorts from 12 high schools in western Washington state, to investigate the influence of multiple disadvantage, four types of discrimination, and protective resources on student physical and mental health and school grades. Results show that both increased multiple disadvantage statuses and experienced discrimination are associated with decrements across outcomes; however, effects are attenuated when protective resources are considered. Yet, as disadvantages mount, the buffering effect of peer and family resources are dampened. No interaction was found between experienced discrimination and protective resources on outcomes.