This thesis primarily aims to provide a solid theoretical understanding behind the incentive structures, decision making and rationality of athletes who decide to utilize doping decisions within a competitive sporting contest. This thesis analyzes the rationality behind eliciting a doping decision, outline a two-stage model of doping in sport in which athletes choose how much to dope and then how much effort to exert, with payoffs determined by an all-pay auction. We also show that a winner-takes-all prize structure leads to maximum effort (when effort can be monitored) but also maximum cheating when it cannot and explore the complimentary idea that people behave more dishonestly in a sporting environment than they do in other environments through theoretical and experimental analysis.