Women working in sport management are underrepresented and face sexism and harassment. While previous research has explained such disproportions and discrimination through examining the behaviors of individual men and women, in this dissertation, I instead examined ways in which sport organizations are “gendered;” that is, how ideas and norms about gender are embedded into sport organizations’ structures and social processes in ways that create and reproduce organizational inequalities. Taking a critical approach grounded in gendered organization theory, I conducted an ethnographic study inside the administrative offices of two men’s professional sports teams. Data include 165 hours of field observations, 29 interviews with participants, and numerous artifacts collected from the field. My findings reveal that the structures of these two organizations are gendered, with men more likely to hold leadership roles as well as positions in departments of greater organizational value, such as sales. Additionally, social practices create further divisions between men and women in the workplace, which I examine in two chapters. In a chapter on dress codes, I discuss how men are empowered by organizational dress while women are challenged and judged by it, their professionalism assessed by the clothing they wear. In a chapter on workplace rituals, I analyze two rituals that reward masculinity and informally exclude women (and some men), and contrast them with a third ritual that emphasizes femininity but faces ridicule from men in the organization. In the final chapter of my findings, I discuss how these structures and practices, in turn, influence staffing decisions: when the organizations downsize their staffs following the COVID-19 pandemic, women are disproportionately impacted by layoffs and furloughs due to multiple, gendered organizational hierarchies. This research furthers understandings of why women are underrepresented in sport organizations, through demonstrating how everyday work practices can advantage men and masculinities. It also contributes to the literature, which has previously highlighted barriers women face during hiring and promotion, through its findings that women face disadvantages during downsizing as well.