This chapter details the results from several research projects related to women in sport and their interaction with social media platforms. The purpose is to provide a comprehensive look at the issues faced by women in sport, athletes, and journalists on social media. We begin by providing a brief background on the media inequities faced by sportswomen. A thematic analysis of audience comments is offered to illustrate the types of engagement various digital presentations motivate among audiences. A sub-case analysis is then presented to explore the phenomenon of fan-generated content relative to women athletes. Finally, we look at the experience of women sport journalists in the digital space. In total, this chapter seeks to provide a deeper understanding of the impact of digital platforms on women’s sport, while generating insight into whether social media have helped or hindered women in sport.