This chapter addresses the issue of doping in cycling. The chapter shows the importance of moving away from considering doping in sport as an individual act of moral failing and towards an understanding of doping as an expected outcome of hypercompetitive sport in the West. The foundations of competitive sport within a capitalist society and how this led to an emphasis on competition and winning are explained to the reader. The relationship between sport, masculinities and doping is then examined before being applied specifically to cycling. The chapter concludes with the argument that the orthodox masculine foundations on which competitive road cycling was developed is a significant factor, amongst others discussed, leading to the environment in which doping became a logical option for cyclists, and thus was consumed into the culture of the sport.