The purpose of this study was to examine the differences of athletes' trust, mental skills associated with athletic performance, and satisfaction in a gambling-legal cycle racing business. A multivariate analysis of variance, using 328 professional racing cyclists in South Korea, showed older athletes (over 40 years old) rated cognition-based trust the highest. The shorter career athletes (1-3 years) rated affect-based trust and mental skills the highest, while a longer career (over 7 years) and the highest class of racing cyclists rated cognitive skills the lowest. The results also suggested that younger athletes (20-29 years old) have higher levels of social satisfaction than older athletes. In addition, athletes with shorter careers rated social and task satisfaction the highest. Finally, we found that longer career athletes had the lowest levels of trust, mental skills, and athlete satisfaction. The results may assist administrators to better understand the important issues of managing athletes in the unique cycle racing business.