Historically, men have dominated the athletic arena; as a result, the number of women in sport management positions has been limited (Cashmore, 2000; Coakley, 2010). Even rarer is the opportunity for female coaches to coach male sport teams. The purpose of this qualitative study was to explore the experiences of women who have coached male athletes. Six female head coaches who had coached or were currently coaching a men's team at the high school (n = 3), college (n = 2), or professional minor league (n =1) level were interviewed, and a cross-case analysis method was used for tagging data and determining themes. Five primary categories emerged: 1) participants had a diversified athletic history; 2) participants had a positive male coaching influence; 3) participants used an intense coaching philosophy; 4) participants felt support from family and athletic administrators; and 5) participants experienced gendering of the coaching role as masculine. Participants suggested that the lack of support systems, mentoring, and networking are the main reasons that the number of women coaching men is so low. Future research should focus on combating the social stigmas in sports administration and coaching. (Contains 2 figures.)