Purpose: The technological advancements in motorcycle road racing have ensured the evolution of motorcycle performance; however, it is unknown whether these advancements have resulted in increased speed and therefore risk. To better understand the top level of this sport and inform future regulations, performance-related strategies, and safety procedures, this study aimed to (1) analyze and describe how the performance characteristics of the top class of the Fédération Internationale de Motocyclisme Grand Prix motorcycle world championship (GPWC) have changed with time and (2) quantify potential interactions between performance data (ie, crashes, speed, and environmental conditions). Methods: Variables such as top 10 riders’ speed of racing, crashes, starting position of winner, participants, and environmental conditions were collected from official race reports from 1997 to 2016. Data standardization was also ensured by including only dry competitions in the analysis. Results: The mean racing speed ranged from a minimum of 155 (7.27) km·h−1 (year 2000) to a maximum of 165 (6.48) km·h−1 (year 2015). Linear mixed-model analysis revealed that the variables year and class significantly influenced changes in mean speed (faster racing). Per race, 12–14% of starters (95% confidence interval) suffered a crash. No significant associations were found between crashes and mean speed, ground temperature, air temperature, or air humidity. Conclusions: The speed of dry racing of the top class of the GPWC has increased over a 20-y span. Motorcycle circuit racing riders should consider the importance of being prepared to cope with crashing events to minimize chances of injury.