Youth with disabilities continue to experience poor post-school outcomes as compared to their peers without disabilities. In this multilevel study, we used an intersectional lens to examine college and career readiness (CCR) among youth with and without disabilities (N = 3523). A CCR assessment yielded four domain scores: Academic Engagement and Processes, Ownership of Learning, Interpersonal Engagement, and Career Development; which were modeled as outcomes of the student- and school-level predictors: race/ethnicity, grade level, and disability status, percentage of White students at school, percentage of students experiencing economic disadvantage, and adverse childhood experiences. Findings show significant student- and school-level variance is explained across the domains. Youth with disabilities scored lower on all domain scores. Results demonstrate the importance of modeling intersecting characteristics to understand the combination of individual and contextual risk factors that may affect CCR for youth and inform collaborative efforts among school staff.