Title IX of the Education Amendments of 1972 (Title IX) prohibits discrimination on the basis of sex in federally funded education programs or activities. Since its enactment, Title IX has dramatically increased interscholastic and intercollegiate athletic opportunities for women and girls. Despite indisputable progress since Title IX’s enactment, particularly for female athletes, many high schools and universities still fail to offer equal athletic opportunities for members of both sexes. Inadequate educational resources for high school and university athletic department administrators leads to a misunderstanding of Title IX’s requirements. This misunderstanding results in institutional misconduct and non-compliance with Title IX. In particular, booster club funds and private donations often result in non-compliance by schools, and administrators who do not understand the scope of the law may not even recognize this non-compliance. Sport-specific booster club funds and privately funded earmarked donations pose a threat to Title IX compliance if administrators allocate these gifts without regard for equitable distribution. To redress disparities between men’s and women’s athletic programs, OCR should offer more robust educational resources and implement Title IX trainings so administrators can prevent misallocating booster club funds and private donations. OCR should train representatives from high school and collegiate athletic conferences to help spread awareness to administrators at their respective institutions. In addition to OCR-mandated trainings, administrators should collaborate with the leaders of their institutions’ booster clubs, alumni associations, and other prospective donors to ensure these individuals recognize the Title IX implications of their gifts. Greater understanding of Title IX is critical for everyone involved throughout the gift-giving process—from the initial donation to the departmental allocation of the funds. Ultimately, if OCR implements more substantive educational resources about Title IX, compliance with the law would improve. This compliance would help ensure equal opportunities are afforded to every student, regardless of sex.