The purpose of this study was to investigate three propositions: a) What are the administration issues most pertinent to interscholastic sport today, as well as the next five years?, b) How important are those administration issues to athletic administrators?, and c) What are the potential implications of those pertinent administration issues to practicing athletic administrators? The literature provides a general overview of relevant issues surrounding interscholastic athletics. However, the importance and implications of relevant issues to practicing high school athletic administrators are difficult to discern. To answer the first proposition, the Minnesota State High School League (MSHSL) provided 10 contemporary administration issues that were most pertinent to interscholastic sport today, as well as the next five years. To answer the second proposition, a Likert-Scale was created so that practicing athletic administrators could rate each issue on a scale of 5 = extremely important to 1 = very little importance. A national study was conducted with athletic directors from the National Interscholastic Athletic Administrators Association (N = 170) annual conference. A one-tailed ANOVA was executed to determine significant differences among the 10 administration issues identified by the MSHSL. Four issues were found to be significant; Athletic Facilities, Athletic Training, Health Issues and Travel Teams. A Games-Howell post hoc was executed to determine significant differences across geographical regions of the United States. For the third proposition, semi-structured interviews were completed to provide insight on the implications for practicing athletic administrators. The results offer insight from which further investigations could be conducted to continue building on policies that influence interscholastic athletic administrators’ day-to-day accountability when overseeing their athletic programs.