College decisions are often the result of a variety of influences related to student background characteristics, academic characteristics, college preferences and college aspirations. College counselors recommend that students choose a variety of schools, especially schools where the general student body matches the academic achievement of students. These types of schools are generally referred to as "match" schools. This thesis examined the initial college decisions of high school students in a large Midwestern state, who were an academic match for selective and highly selective schools by observing the student characteristics that were most influential in predicting college matching for students' initial first choice institution. This thesis also observed college enrollment among students who chose a match school as their first choice institution, college matching over a time period from 1992 to 2013, and college matching after the implementation of a state initiative designed to help students apply for college. Logistic regression along with descriptive statistics were used as the primary analyses for college matching. Results from these analyses showed that students belonging to underrepresented minority groups had odds of college matching for their first choice institution that were significantly greater than white students. Students whose parents earned at least a bachelor's degree had odds that were significantly greater than students whose parents had not earned a bachelor's degree. Also, students whose coursework included calculus and physics, and students who planned to earn a graduate degree had significantly greater odds of matching on their first choice institution than students who were not a part of these respective groups. Among students in the sample who chose a match school for their first choice institution, students who had at least one parent earn up to a bachelor's degree were significantly more likely to enroll in a match school. Also, the percentage of students at a single high school who were eligible for free and reduced lunch were negatively associated with the odds of students enrolling in a match school. To observe score sending among students to their first choice institution over time an additional variable, "year" was added to the logistic regression model to compare the years of 2000, 2008 and 2013 to 1992. The results of this logistic regression analysis showed that students' odds of choosing a match school for their first choice institution were significantly lower in 2008 and 2013 than in 1992. College matching for students who attended high schools serviced by the state initiative were compared using the percentage differences in college matching before and after the implementation of the program. However, results could not be interpreted with certainty due to the small size of the sample. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]