Despite the advancement of explicit legal protections for transgender/transsexual/transitioned people in many Western nations around the world, sport remains a contentious domain for trans and other gender-variant people. This chapter examines five exceptional athletes, from around the world, who are breaking gender boundaries in their sports. Regardless, each of the five athletes highlighted within the chapter have gone through great lengths to live authentically – both as athletes and advocates for equity, justice, and human rights in sport. Although the LGPA's move toward trans inclusion was seen as a win for civil rights, trans golfers, and trans athletes more broadly, Mianne Bagger, the first trans woman to qualify for the Ladies European Tour in 2004, publicly expressed her frustrations with Lawless. Overwhelmingly, though, trans athletes are making much advancement in sporting inclusion policies, most notably at the Olympic level.