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. In 2001, he had a narrowing in the iliac artery. Tests showed his right leg produced more power than his left. After surgery in April 2002, he was again in contention in the 2002 Tour de France. In 2003 and 2004 he was overshadowed in the green jersey competition by fellow Australian sprinters Baden Cooke (2003) and Robbie McEwen (2004). O'Grady still managed to win his second Tour de France stage, in 2004. O'Grady moved to in 2004 to concentrate on races such as Paris–Roubaix and the Tour of Flanders. After a start fraught with injuries and doping allegations in his team, he won two stages and the points classification in the Critérium du Dauphiné Libéré. He won a stage in the 2004 Tour de France and spent a few days in the green jersey. He won the UCI Road World Cup race, HEW Cyclassics. He topped his victories by winning an Olympic gold medal in the madison cycling with Graeme Brown. In the 2005 Tour de France, O'Grady came second in the green jersey classification to Thor Hushovd of Norway, followed by Robbie McEwen. Late in 2005, he signed a one-year contract with Bjarne Riis to ride on , now known as Saxo Bank, for 2006. He broke several ribs in an early season race in Italy and a vertebra in the Tour de France. O'Grady continued riding the Tour despite the pain, coming third in the final stage. Early in 2007, O'Grady became the first Australian to win a major classic when he crossed the line first in Paris–Roubaix. He had a puncture midway but recovered to rejoin the field before arriving alone in the Roubaix Velodrome. On 15 July 2007, O'Grady was forced to abandon on stage 8 of the 2007 Tour de France, from Le-Grand-Bornand to Tignes, after crashing on a descent, fracturing eight ribs, his right shoulder blade, right collar bone and three vertebrae, and puncturing his right lung. O'Grady crashed into the 2009 Milan–San Remo when another rider came down in front of