In the men’s event, Daniil Medvedev’s title defence came to an end after he fell to a 6-1 6-4 defeat by American 14th seed Tommy Paul.

The Russian’s exit means world number five Alexander Zverev, who beat Portugal’s Nuno Borges 6-2 7-5 on Thursday, is the highest-ranked player left in the draw.

World number two Jannik Sinner and third-ranked Carlos Alcaraz withdrew because of injury before the event, while top seed Novak Djokovic was knocked out by Alejandro Tabilo in the second round.

Tabilo followed up his surprise win over the Serb by upsetting Russian 16th seed Karen Khachanov.

The Chilean, ranked 32nd in the world, won 7-6 (7-5) 7-6 (12-10) to reach his first ATP Masters 1,000 quarter-final.

He will play China’s Zhang Zhizhen, who defeated Brazilian qualifier Thiago Monteiro 7-6 (7-4) 6-3.

Meanwhile, Greek sixth seed Stefanos Tsitsipas needed just 61 minutes to thrash Australia’s Alex de Minaur 6-1 6-2.

Tsitsipas, a finalist in Rome in 2022, has lost just two of his 15 matches on clay this season.

The Monte Carlo champion and Barcelona Open finalist will face Chile’s Nicolas Jarry, who beat Frenchman Alexandre Muller 7-5 6-3.

American Taylor Fritz overcame Bulgarian eighth seed Grigor Dimitrov 6-2 6-7 (11-13) 6-1 after letting a match point slip during a 20-minute second-set tie-break.

Fritz, the 11th seed, will now take on Zverev, while Paul’s victory over Medvedev means he will face Poland’s Hubert Hurkacz in the last eight.

Hurkacz fought back from a set down to beat Sebastian Baez of Argentina 5-7 7-6 (7-4) 6-4.