Women in athletic training face barriers when working with male sports teams; the reasons are multifactorial, including traditional sex stereotyping and the social networking of male leaders (i.e., the “old boys club”). The purpose of our qualitative research study was to explore the experiences of women athletic trainers providing medical care to a male athletic team within the collegiate setting. Fifteen female NCAA Division I collegiate athletic trainers working with male sports teams completed telephone interviews. The interpretative phenomenological analysis approach was utilized. Trustworthiness was ensured through peer review, multiple researcher triangulation, and saturation. Participants experienced discriminatory behavior, sexism, and gender bias within the workplace. Though their relationships with student-athletes and coaches were often harmonious, participants experienced sexism and discrimination from the time they were students through their professional careers.