In the 1998 Tour de France, a race for which he confirmed to doping himself with illicit and proscribed erythropoietin, he wore the yellow jersey for three days. He also won his first stage. In 2001 he wore the yellow jersey for six days. He was "Australian Cyclist of the Year" and "Australian Male Road Cyclist of the Year" in 1998 and 2001. In 1998 he finished second in the green jersey classification. On 6 July 2000, he pulled out of the Tour de France after breaking his collarbone in three places with to the finish, he still finished the stage. In 2001, O'Grady had been in contention for the green jersey with Erik Zabel but he was defeated on the final day.