Women’s sport has recently seen historic growth across the United States as new leagues launched and existing leagues reached new heights. Despite notable wins, sport remains a male-dominated institution and women’s sport does not always receive the respect it deserves. Indeed, evidence suggests women’s sport is devalued, enduring a unique stigma. Thus, the purpose of this dissertation is to explore the impact of stigma on fans of and employees working in women’s sport. I do this through three studies. In Study 1, I use reflexive autobiography to begin to develop a theoretical understanding of women’s sport fans’ experiences with stigma and empowerment. I document vignettes from a decade of fandom, focusing on my experiences with the Phoenix Mercury. In doing so, I identify how I observed structural stigma and experienced enacted, felt, and internalized stigma, as well as how my fandom facilitated a sense of optimal distinctiveness. Study 2 builds on the understanding of stigma in women’s sport to explore employees’ experiences working in an occupation that may be considered ‘socially dirty.’ Using a case study methodology, I conducted semi-structured interviews with 15 employees in women’s sport. I find that women’s sport employees observe structural stigma and personally experience enacted, felt, and internalized stigma. I subsequently identify strategies women’s sport employees use to navigate this work-based stigma, finding they utilize a necessity shield, as well as engage in and with meaningfulness, job crafting, and social weighting. Study 3 builds on the earlier studies to examine the labor of being a women’s sport fan. This labor is in part a function of women’s sport operating outside the broader cultural consciousness—a form of stigma to which these fans are well attuned. Thus, I conducted a multi-wave field study of sport fans to understand the influence of structural stigma on fan emotions and behaviors. I find that fans of women’s sport engage in loyal boosterism, a process mediated by perceptions of structural stigma and subsequent experiences with stigma-related stress. Collectively, these studies help further develop an understanding of the unique theoretical context of women’s sport, given the stigma with which it contends.