Federer again, 5–7, 6–7, 6–7. At Wimbledon, he surprised the tennis world by reaching the fourth round on his least preferred surface. Moving to the hard-court season in the US, Davydenko had strong showings in the Canada Masters and the Cincinnati Masters, reaching the quarterfinals and semifinals, respectively. Davydenko then reached the semifinals of the U.S. Open for the second consecutive year, before losing to Roger Federer, 5–7, 1–6, 5–7. He won his eleventh career title in Moscow, defeating Paul-Henri Mathieu. In November, he took part in the Masters Cup, which took place in Shanghai, China. He played in the Red group round robin, losing to eventual champion Roger Federer 2:0 sets, losing to Andy Roddick 2:1 sets, and beating Fernando Gonzales 2:0 sets, thus finishing 3rd in the group, meaning he did not reach the knockout stage. Davydenko ended the year ranked no. 4 and in the top 5 for the third straight year. 2008 Davydenko started 2008 at the Australian Open, where he was seeded fourth. He won his first three matches in straight sets, but in the fourth round he lost to countryman Mikhail Youzhny, 6–7, 3–6, 1–6. In Dubai, he reached the semifinals, losing to Feliciano López in three sets. He then went on to win his biggest career title to date at the Miami Masters. En route to the win, he defeated Andy Roddick in the semifinals and Rafael Nadal, 6–4, 6–2, in the final to win his second ATP Masters Series title. His win over Roddick in the semifinals was his first victory in six matches, while his win over Nadal was his first in three matches. Davydenko began the European clay-court season with a final appearance in his next tournament, the Estoril Open in Portugal, where he met world no. 1, Roger Federer in the final. In the second set of the final, while trailing Federer, 6–7, 2–1, Davydenko retired with a left leg injury. He then reached the semifinals of the Monte Carlo Masters. He won his thirteenth career title in Pöertschach, defeating Juan Mónaco, 6–2, 2–6, 6–2. After a disappointing French Open, Davydenko went on to win another title, this time in Warsaw, defeating Tommy Robredo, 6–3, 6–3, in the final. Appearing at the 2008 Summer Olympics, Davydenko's stay in Beijing was brief; despite being seeded fourth at the Games, he would be upset by Paul-Henri Mathieu in the second round.