Simple Summary: The disease osteochondrosis dissecans (OCD) is an important health-related trait in horse breeding. This study aimed at finding a breeding strategy to reduce the occurrence of OCD without affecting the riding horse performance traits substantially. Therefore, a lifelike simulation of different possible ways to include this trait in a horse breeding program was performed. Effective strategies can be the exclusion of affected animals from breeding as well as the selection based on a breeding value estimation which considered OCD susceptibility together with riding horse performance traits in an index. A reduction in the frequency of occurrence of OCD was found to be linked with a slight decrease in the breeding values for the riding horse characteristics.