We explore the shifting gender relations of sport that shape, and are shaped by, various forms of digital mediation (production, consumption, organization, and management). The sport-media industrial complex has evolved through historically gendered relations that intimately connect the physical and digital dimensions of sport at community and elite levels which impact the growth of women's sport. While women's elite sport has benefited from the digitization of sport with the proliferation of social media platforms (and some related investment in mainstream coverage), it would be naive to narrate such change as a linear progress narrative of greater empowerment. Our chapter draws upon feminist analysis research into the gendered algorithmic formation of digital spaces and representations in contemporary society, alongside research on women athletes and social media across sport management and sociology. We offer global case study examples, to explore the shifting gender power relations challenging historically masculine representational and management practices. We discuss the complexities of how digital practices work to obscure gender inequities and long-held assumptions about gendered bodies and binaries that underpin sport. We ask, what are the lessons to be learned for sport organizations as they navigate changing gender dynamics in the digital future of sport?