In 2007, the Virginia Board of Education directed the Virginia Department of Education (VDOE) to study academic indicators that are associated with high school students' successful preparation for college and careers. VDOE then embarked on a multi-year effort to identify available data sources and conduct research on high school indicators that are associated with enrollment and success in credit-bearing courses in college. VDOE's initial studies linked high school indicators with students' enrollment in four-year colleges and universities across the country that was acquired from the National Student Clearinghouse. This report is the first in a two-part series connecting high school program and outcomes data to course enrollment, grades, and persistence in Virginia's two- and four-year institutions of higher education (IHE). This first report addresses the following questions: (1) How did students who enroll in Virginia two- and four-year colleges differ from those with no record of enrollment in a Virginia college?; (2) To what extent were better prepared students less likely to enroll in developmental courses?; (3) To what extent did better high school academic preparation close income and ethnic gaps in student enrollment in developmental courses?; (4) To what extent were better prepared students more likely to persist into their second year in the Virginia higher education institution in which they enrolled in the first year?; and (5) To what extent did better high school preparation close income and ethnic gaps in second-year persistence? Following a brief description of the high school and higher education data files used in the analysis, the remaining sections of this report address each of these five questions. Throughout the report, the authors present both descriptive statistics that compare higher education outcomes for different groups of students, and results from statistical analyses that estimate the incremental association between a given high school variable and higher education outcomes after controlling for other variables. Appended are: (1) Match Procedure and Diagrams; (2) Technical Material for Multivariate Analyses Section; (3) Multivariate Logistic Regression Estimates for Research Objective I; (4) Multivariate Logistic Regression Estimates for Research Objective II; (5) Predictive Accuracy of the Algebra I and Algebra II SOL: Classification Table Results; and (6) References. (Contains 8 tables, 25 figures and 22 footnotes.)