Homeless and low-income students share multiple overlapping risk experiences; however, some studies report little to no observed differences in outcomes between these students. From the cumulative risk perspective, homelessness is perched at the extreme edge of economic insecurity, suggesting that homeless students encounter additional hardships beyond poverty experiences alone. Using a continuum of risk framework, this study leveraged statewide administrative data from a 6th grade cohort of Maryland public school students (N = 52,610) to investigate the association between homelessness and educational and early labor market outcomes, above and beyond the associations linked to poverty. Findings provide support for the continuum of risk in relation to educational outcomes; however, no significant differences were observed in early labor market outcomes, although racial differences were detected. This study underscores the importance of targeted interventions in promoting positive, long-term outcomes, particularly for students who were homeless in adolescence.