As ‘contractors to contest’, athletes must accept certain constraints, such as that against doping, in order to count as acceptable opponents. This essay is an attempt to explore the issue of doping in sport via applied ethics, showing how complicated and messy individual cases can be, and how our judgements about them are coloured by a range of moral possibilities and intersecting contextual features. Sometimes there just aren't any clear-cut answers. It examines four recent cases involving UK athletes, which present us with different though overlapping features, opening up a wide range of issues for consideration. It explores the adequacy and morality of the actions of the athletes and their support teams, and of certain rules, procedures, decisions and judgements surrounding these cases