France’s Hugo Gaston stunned ninth-ranked Alex de Minaur in three sets to record his first career top 10 win and make the semi-finals of the Antwerp ATP tournament on Friday.

The 77th-ranked Gaston came through against the top seed 6-3, 3-6, 7-5 to register his second win over the Australian having also prevailed at the 2022 French Open.

“It was really close,” said Gaston.

“Alex is such a great player, playing unbelievable tennis this year and in the past few years.”

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Gaston will next face Spain’s Roberto Bautista Agut who defeated third seed Felix Auger-Aliassime of Canada 3-6, 6-2, 7-6 (8/6).

Second seed Stefanos Tsitsipas was also knocked out on Friday, losing to 33rd-ranked Jiri Lehecka of the Czech Republic, 6-4, 6-4.

Appearing in his 14th tour-level quarter-final, 22-year-old Lehecka hit 19 winners, including eight aces and did not face a break point.

The fifth seed will play either Marcos Giron of the United States or Sweden’s Zizou Bergs for a place on the final.

Elsewhere, three-time Grand Slam champion Stan Wawrinka rolled back the years, ousting top seed Andrey Rublev to reach the Stockholm semi-finals.

Wawrinka, currently ranked 217th in the world, battled past seventh-ranked Russian Rublev, 7-6 (7/5), 7-6 (7/5) to notch his first win over a top-10 player this year.

The Swiss player next meets US fourth seed Tommy Paul, the 2021 Stockholm champion, who beat Serb Miomir Kecmanovic 7-6 (9/7), 6-2.

“I cannot change my age, but most important for me is that when I enter the court, I always try to fight,” said Wawrinka, the third-oldest semi-finalist in modern ATP Tour history behind Jimmy Connors and Ivo Karlovic.

“I try to improve and enjoy what I am doing. The reason I keep going is to play matches like this, with so many people giving me good energy on the court, and I’m super happy to have the chance to play one more match tomorrow.”

The former world number three fired down 14 aces, converting his first match point to reach the semi-final in the Swedish capital for the first time in four attempts.

“The key was to stay focused and positive with myself,” said Wawrinka, who had let a 2-0 lead in the second set slip.

He is bidding for his 17th ATP title and first since Geneva in 2017.

Wawrinka won the Australian Open in 2014, the French Open in 2015 and the US Open in 2016.