Roger Federer defeated Andy Roddick with 5-7 7-6 (8-6) 7-6 (7-5) 3-6 16-14 in the Finals of Wimbledon 2009. Roger Federer defeated Andy Roddick to surpass Sampras’s 14 Grand Slam wins and sixth Wimbledon title that he lost to Rafael Nadal last year. No Tears from Federer this time who made history in the Grand Slam by winning 15 major titles.