Stefanos Tsitsipas has found defeat at the hands of 14th seed Karen Khachanov, the Russian’s first win over the Greek in their seven meetings, taking down the world No.3 7-6 (7-4) 6-4 in the fourth round to end a 23-match winless run against top-10 opponents.

Tsitsipas, who got a first-round bye and second-round walkover, beat Cristian Garin in his Miami opener but never found his best level against Khachanov, who controlled the match by winning almost 90 per cent of his first-serve points.

“They say third time is a charm, but for me it took seven times, so I’m super happy,” said Khachanov, who lost to Tsitsipas in the semi-finals of this year’s Australian Open.

Khachanov will next play Francisco Cerundolo, a semi-finalist in Miami last year, while another Russian in fourth seed Daniil Medvedev was forced to start late and off his scheduled court after a three-hour rain delay to beat Quentin Halys of France 6-4 6-2.

He will face American Christopher Eubanks, who edged Adrian Mannarino in a pair of tiebreakers.

Indian Wells champion Carlos Alcaraz remains on course to complete the ‘Sunshine Double’ with a straight-sets wins at the Miami Open over Tommy Paul.

His task has been made easier by the removal of second seed Tsitsipas, sent packing by Khachanov on Tuesday.

Spain’s world No.1 deployed his dynamic game to tame Paul 6-4 6-4 and set up a quarter-final against another American Taylor Fritz, who eased past Denmark’s Holger Rune 6-3 6-4.

“I’m really excited for it,” Fritz said.

“I think that a lot of people are really excited for that, too.”

Paul, who came from behind to beat Alcaraz in their only previous meeting at last year’s Rogers Cup, fended off a first match point while serving at 5-3.

But there would be no escape from Alcaraz, the top-seeded teenager letting out a mighty roar when Paul’s forehand missed to end the contest.

“The key of that match was that I was playing to attack,” Alcaraz said.

“I didn’t let him play his game – attack and go to the net. I did those things first … I played a really complete match.”

Alcaraz is now three wins away from the ‘Sunshine Double’ after his victory at Indian Wells last week, something he needs to do to retain his top ranking from Novak Djokovic.

Elsewhere, Italian 10th seed Jannik Sinner breezed past sixth-seeded Andrey Rublev, firing off more than two dozen winners to win 6-2 6-4.

He next faces Emil Ruusuvuori after the Finn beat 26th seed Botic van de Zandschulp of the Netherlands 4-6 6-4 7-5.