only his 4th tournament since coming back from injury; he had to default against Radek Štěpánek, another player coming back from injury, because of an injury sustained during his quarter-final win. He also made an impressive showing at the 2007 Madrid Masters, where he beat number five seed Fernando González in the quarterfinals before losing in the semifinals to world number one Roger Federer 6–4, 6–4. 2008 His 2008 season did not start out well: he lost in the first round of the Australian Open to former world No.1 Juan Carlos Ferrero, first round of 2008 Indian Wells Masters to Dudi Sela, third round of 2008 Miami Masters to world No.2 Rafael Nadal, second round of 2008 Monte Carlo Masters to Philipp Kohlschreiber, first round of 2008 Rome Masters to Ferrero. His first notable result was the quarterfinals of the 2008 Hamburg Masters with victories over world No.10 Stanislas Wawrinka and world No.4 Nikolay Davydenko before losing to Andreas Seppi in three sets. He would lose in the third round of 2008 Wimbledon Championships to Nadal. During the 2008 Canada Masters, at age 31 and ranked No. 37, he made his first Masters final after 73 previous tries, previously finishing as a semifinalist at the 1999 and 2004 Canada Masters (lost to Thomas Johansson and Andy Roddick respectively) and 2007 Madrid Masters (lost to Federer). Along the way, he defeated Mardy Fish, 15th seed Mikhail Youzhny, fourth seed Nikolay Davydenko, seventh seed James Blake, and Gilles Simon; the win over Simon was especially notable because Simon had defeated world No. 1 Roger Federer in the second round. He lost to Nadal in the final in straight sets. Because of his run, he broke back into the top 20 at No. 19. 2009 In 2009, he represented Germany in the 2009 Hopman Cup with 19-year-old Sabine Lisicki. In the first match, he lost against Australia's Lleyton Hewitt, who had been six months inactive due to an injury. In the second singles match, Kiefer lost again, this time to USA's James Blake. Nevertheless, Kiefer won both of the doubles matches with Sabine Lisicki against both Australia and the United States. In the third singles match, Kiefer twisted his ankle against Slovakia's Dominik Hrbatý in the first set when Kiefer was up 3–1 and serving. This injury prevented him from participating in the 2009 Australian Open. He re-appeared in the 2009 Davis Cup