Number eight seed Janko Tipsarevic has been defeated in four sets by 26th-seeded Russian Mikhail Youzhny, losing 6-3 6-4 3-6 6-3.
A single break early in the first set was enough to see the Russian into a lead with some powerful shots proving too strong.
The second set followed the same story, as Youzhny broke Tipsarevic again in the third game, which was enough to take him into a commanding lead.
The Serbian finally managed a break of his own at the first time of asking in the third set, and held his serve comfortably to pull a set back.
However, the Russian finished strongly, taking the final set 6-3 and knocking out the Serb who had looked comfortable so far in the tournament.
