This chapter evaluates the role of the law in the support of the wellbeing of athletes. Whilst the essence of sport encompasses an element of differential treatment to separate winners and losers, the inclusion or exclusion of athletes in competitive sport potentially causes tensions between the interests of sport and the human rights of the athlete. This chapter will be centred on British female canoeist, Samantha Rippington, who launched a legal challenge against the London Organising Committee of the Olympic and Paralympic Games (LOCOG), because of the absence of women’s canoe racing events in the programme. She was supported by WomenCAN International, a leading global advocate for equality and equity in Olympic canoeing. The President of WomenCAN International, Pam Boteler, will also feature, offering unique insights into the role that her organisation played in this action. Sam’s case highlights the unique challenges that athletes face when seeking a legal remedy, and the personal struggle that Sam encountered during her fight for inclusion. The chapter will offer recommendations for athlete support through legal action.