The Illinois Skyway Collegiate Conference (ISSC) is unique in that there must be participation in athletic and co-curricular competitions each year. Established in 1969 as an athletic conference, ISSC states in the bylaws (2016) that there is a commitment to fostering the development of students' specialized talents through intercollegiate athletic and co-curricular programs. Activities must be based upon sound educational philosophy, which enhance student academic achievement, promote fair play, and develop mental and physical abilities. Each year, students from eight colleges participate in co-curricular and athletic competitions. Athletic sports hosted are women's basketball, cross country, soccer, softball, tennis, and volleyball, and men's basketball, baseball, cross country, golf, soccer, and tennis. Athletics, student affairs, academic affairs, and administration are encouraged to interact to fulfill the institutional commitment. Members of the ISSC include the College of Lake County, Elgin Community College, McHenry County College, Moraine Valley Community College, Morton College, Oakton Community College, Prairie State College, and Waubonsee Community College. This article begins by describing the yearly assessments that are completed to learn how the co-curricular activities influenced retention, persistence, and student engagement. It goes on to discuss how feedback from participants can be used by the next host school, unique implementation challenges that each college faces, and potential challenges and benefits of the program.