In later years, most of Hewitt's best results have come at grass court tournaments, although he did reach the quarterfinals of the 2009 Cincinnati Masters and also won the 2014 Brisbane International, defeating Roger Federer in the final. At the 2009 Wimbledon Championships, Hewitt defeated Juan Martín del Potro en route to his first grand slam quarterfinal in three years where he lost in five sets to the eventual runner-up, Andy Roddick. The following year, Hewitt recovered from a set down to defeat Federer in the final of the Gerry Weber Open, thus ending his 15-match losing streak against the Swiss dating back to 2003. Between July 2012 and July 2014, Hewitt reached three consecutive finals at the Hall of Fame Open, losing to John Isner and Nicolas Mahut respectively before winning the title for the first time with a three set win over Ivo Karlović.
