Although it is not generally applauded, withdrawing from competition is sometimes the best available option. However, an individual withdrawal may generate external costs that affect people other than the withdrawing individual. As cycling finances increase worldwide, the losses that are incurred due to riders’ withdrawals assume a rising importance. Therefore, we test the determinants for professional riders’ withdrawals by using probit estimations on nine major races (Le Tour de France, La Vuelta, Il Giro, the Tour de Suisse, the Tour of Poland, the Tour de Picardie, Paris-Nice, Tirreno-Adriatico, and Critérium). Our results recognized that riders withdraw because of a combination of factors, such as individual circumstances (such as a rider’s age or a dense body mass index), each race’s orography and a low overall placement. These results indicate that teams that seek to minimize this source of losses have to manage riders’ expectations, rightly choose the races in which to participate and optimize the team members’ interactions with each other.