Adrian Mannarino earned his biggest win by Pepperstone ATP Ranking on Thursday when he upset World No. 3 Daniil Medvedev 4-6, 6-4, 6-2 at the Libema Open.

The Frenchman, who won the title at the ATP 250 grass-court event in ‘s-Hertogenbosch in 2019, caused Medvedev problems with his flat groundstrokes throughout the two-hour clash. He timed the ball cleanly off both wings and returned with depth, avenging his semi-final defeat against Medvedev at last year’s event.

Mannarino has now captured nine Top 10 wins, with his victory against Medvedev his second against a Top 10 opponent on grass. The 34-year-old also defeated then-World No. 5 Dominic Thiem in Mallorca in 2021.

Medvedev has won a Tour-leading five titles this season but struggled with his consistency against Mannarino, who pulled the top seed around the court with an array of angles.

Into his third quarter-final of the season, Mannarino will next meet Jordan Thompson. The Australian triumphed 7-6(4), 6-1 against Canadian Milos Raonic, who was making his return to Tour this week after two years out.

In earlier action, sixth seed Tallon Griekspoor moved past Australian Alexei Popyrin 6-3, 6-2 to reach his fourth tour-level quarter-final of the season. The Dutchman will continue to lead home hopes when he faces Alex de Minaur in the last eight. The Australian beat Laslo Djere 6-1, 6-7(5), 6-3.