In this study, we compared the perspectives of students' 21st-Century competencies (critical thinking and communication, applied learning, and intrapersonal and interpersonal skills) based on participating in an urban magnet information technology (IT) career academy compared to a traditional, comprehensive high school. We utilized propensity score matching to match academy and comprehensive high school learners on various demographic variables. The propensity score matching resulted in 299 matched pairs (n = 598). Using the matched groups, we ran linear regression models to investigate the relationship between school participation and students' perceptions of their 21st-Century skill attainment. We found that when compared with their comprehensive school peers, academy students believed their schools significantly contributed more to their abilities to apply knowledge from their coursework to a real-world context. We found no significant differences in critical thinking and communication skills as well as intrapersonal and interpersonal skills. Our findings indicate that the nature of the curriculum and instructional strategies within a career academy are beneficial. These strategies include the use of curriculum integration, work-based learning, and project-based learning to increase the meaningfulness and relevancy of content.