In 2007, the Illinois General Assembly passed the College and Career Readiness Pilot Act that supported the initial implementation of college readiness programming by community colleges and their high school partners. This study uses mixed-methods research to examine program implementation and student outcomes associated with two of seven college and career readiness (CCR) partnerships in Illinois. Our analysis of the local models is guided by Conley’s four dimensions of CCR, and the results shed light on how different programmatic approaches contribute to short-term student outcomes in mathematics and English. This study has implications for Illinois’ efforts to move CCR forward, including for the state’s new Race to the Top (RttT) grant that is attempting to scale up CCR programming associated with science, technology, engineering, and mathematics (STEM) education.