Tipsarevic upset by Russian teen
Seventeen-year-old Karen Khachanov stunned third seed Janko Tipsarevic to reach the quarter-finals of the Kremlin Cup.
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The teenage Muscovite, ranked 808th in the men's singles rankings, beat the 27th-best player in the world in straight sets, closing out a 6-4 6-4 win in little over an hour.
Khachanov hit 14 aces past two-time US Open quarter-finalist Tipsarevic, 29, and did not face a break point.
Next up for the prodigiously talented Russian in his home city will be either Ivo Karlovic or Denis Istomin.
The former came through his first-round meeting with Denis Kudla with relative ease (6-2 6-3) but Istomin needed three sets to eliminate Andrey Kuznetsov 6-0 2-6 6-1.
Kazakhstani qualifier Andrey Golubev surprised another top seed to reach the last eight, dispatching the sixth-seeded Horacio Zeballos 6-3 6-4.
Edouard Roger-Vasselin will meet second seed and reigning champion Andreas Seppi in the other confirmed quarter-final after both men sealed straight-sets wins.
France's Roger-Vasselin ousted Sergiy Stakhovsky 7-5 7-5 while Seppi beat fellow Italian Paolo Lorenzi 6-3 6-2.
Eighth seed Adrian Mannarino made an early exit, losing his opening match 3-6 6-4 6-4 to Teymuraz Gabashvili.
There was a big shock in the women's draw as home favourite Maria Kirilenko lost 6-3 6-3 to Anastasia Pavlyuchenkova.
The third seed may have missed out on the quarter-finals but Russia's interests were kept alive by Alisa Kleybanova and Svetlana Kuznetsova, who beat Carla Suarez Navarro and Sofia Arvidsson respectively.
Elena Vesnina was not so lucky as Italian second seed Roberta Vinci rallied from a set down to triumph 2-6 6-1 6-4.
Elsewhere, Sam Stosur booked a second-round meeting with Alize Cornet by seeing off Kaia Kanepi 6-3 6-1.