Monte Carlo - Eighth seed Janko Tipsarevic of Serbia suffered another early exit when he was beaten 7-6 6-1 by Bulgarian Grigor Dimitrov in the Monte Carlo tennis second round on Tuesday.
World number 10 Tipsarevic, who has never made it past the third round at the clay-court Masters series event, extended his poor win-loss record to 2-6 since he reached the Australian Open last 16 in January.
The 21-year-old Dimitrov, regarded as one of the most gifted prospects on the tour, recovered from a break down in the first set then easily prevailed in the tie-break, wrapping it up with a subtle backhand pass.
The 34th-ranked Bulgarian then cruised to his first win of the season over a top-10 player to reach the last 16.
Results from the third day of the Monte-Carlo Masters on Tuesday (x denotes seeding):
Albert Ramos (ESP) bt Radek Stepanek (CZE) 6-3, 6-3
Stanislas Wawrinka (SUI x13) bt Denis Istomin (UZB) 6-3, 7-5
Marinko Matosevic (AUS) bt Fernando Verdasco (ESP) 7-5, 6-3
Grigor Dimitrov (BUL) bt Janko Tipsarevic (CRO x8) 7-6 (7/3), 6-1