The purpose of this study was to investigate three research questions: (a) What are the ethical issues most pertinent to interscholastic sport today, as well as in the next 5 years? (b) How important are those ethical issues to interscholastic athletic administrators? (c) What are the potential implications of those pertinent ethical issues to practicing interscholastic athletic administrators? For the first inquiry, the Minnesota State High School League (MSHSL) provided 14 contemporary ethical issues that were most pertinent to interscholastic sport today, as well as in the next 5 years: behavioral issues, competing club sports, competitive balance, emphasis on winning, health concerns, nontraditional sports, outside sport organizations, participation for all, pay-to-play organizations, promises by camp organizers, scholarship myth, sportsmanship, too much structure, and win at all costs. For the second proposition, a national study was conducted with athletic directors from the National Interscholastic Athletic Administrators Association (n = 170) annual conference. Following a survey in which participants ranked issues according to importance, a one-tailed analysis of variance determined significant differences among the 14 ethical issues identified by the MSHSL. Four issues exhibited significant differences based on region: behavioral issues, promises by camp organizers, scholarship myth, and win at all costs. A Games-Howell post hoc determined significant differences across geographical regions of the United States for these four ethical issues. For the third research question, semistructured interviews provided insight on the implications for practicing athletic administrators. Athletic administrators generally emphasized the importance of the issues identified in this study.