Top seed Andrey Rublev crashed out of the St Petersburg Open after a straight-sets defeat by Dutch qualifier Botic van de Zandschulp in the quarter-finals.

A recent US Open quarter-finalist, world number 69 Van de Zandschlup claimed the first top-10 win of his career on Friday.

The 26-year-old also advanced to the semi-finals of an ATP event for the first time.

There, he will face 2011 champion Marin Cilic, who was a 6-4 3-6 6-3 winner over third seed Roberto Bautista Agut.

Denis Shapovalov was another big-name casualty in Russia, the second seed going down 4-6 3-6 against world number 53 Jan-Lennard Struff.

Although, there were better fortunes for fifth seed Taylor Fritz. The Indian Wells semi-finalist is yet to drop a set this week after prevailing 6-4 6-2 against John Millman.

Elsewhere, Matteo Berrettini was the victim of another upset at the Erste Bank Open in Vienna.

The Wimbledon champion went down 1-6 7-6 (7-2) 6-7 (5-7) following a two-hour 40-minute battle with Carlos Alcaraz.

Reaching his first ATP 500 semi-final, the Spanish teenager claimed another big scalp having defeated Stefanos Tsitsipas at Flushing Meadows last month.

However, second seed Alexander Zverev remained on course for a fifth title of the season, as he claimed his 300th tour-level win.

The Australian Open finalist beat Felix Auger-Aliassime 6-4 3-6 6-3, avenging his fourth-round defeat by the Canadian at Wimbledon in July.

Alexander Zverev and Jannik Sinner moved into the quarter-finals of the Vienna Open on Thursday. 

Italian Sinner beat home hopeful Dennis Novak 6-4 6-2 to set up a tantalising showdown with Casper Ruud. 

Should he win that match, Sinner will move ahead of Hubert Hurkacz in the race to qualify for this year's ATP Finals, while victory for Ruud will strengthen the Norwegian's standing. 

"It's going to be tricky," said Sinner. "He's in a better position than I am for the race. I think right now it's tough to say and tough to do because in the end you try always not to think about that, but in the end you think about that because you believe." 

Zverev was given a sterner test, eventually overcoming Alex de Minaur 6-2 3-6 6-2 in one hour and 42 minutes. The Olympic gold medallist will now face Felix Auger-Aliassime, who fought back from a set down to defeat Cameron Norrie. 

Frances Tiafoe came from a set down to upset top seed Stefanos Tsitsipas 3-6 6-3 6-4 and earn a quarter-final meeting with Diego Schwartzman after the Argentine overcame Gael Monfils 7-6 (7-5) 4-6 6-2. 

In St Petersburg, home favourite and sixth seed Karen Khachanov lost a gruelling three-set encounter to Marin Cilic. 

The Croatian, who won the title in Russia in his last appearance in 2011, was 4-1 down in the deciding set but took all five of the final games to triumph after two and a half hours on court. 

"Everybody is playing good. The tournament is great. It's the end of the season, so everybody wants to finish on a great level," said Cilic, who next faces Roberto Bautista Agut. "For me, it was great to play this kind of a match today." 

Another Russian, Aslan Karatsev, fell to John Millman 6-3 6-2. Taylor Fritz and Botic van de Zandschulp also progressed in straight sets. 

Jannik Sinner continued his push for an ATP Finals spot with a straight-sets defeat of Reilly Opelka in the first round of the Vienna Open, while Carlos Alcaraz exacted revenge on Andy Murray.

Sinner won his fourth title of what has been an outstanding season for the Italian in Antwerp last weekend and is only 110 points adrift of Hubert Hurkacz in the battle for the final place in the season-ending event in Turin.

Murray did the 20-year-old a favour by knocking Hurkacz out of the ATP 500 tournament in the Austrian capital on Monday and seventh seed Sinner eased to a 6-4 6-2 win over American Opelka two days later.

Sinner, who will overtake Pole Hurkacz if he reaches the semi-finals this week, won 93 per cent of points behind his first serve and did not face a break point in a resounding win and will play Dennis Novak in the second round.

Murray beat Alcaraz at Indian Wells this month, but the 18-year-old rising star from Spain turned the tables on the three-time grand slam champion with a 6-3 6-4 second-round win in Vienna.

Former world number one Murray struggled with his serve and was broken five times as he made an early exit.

Third seed Matteo Berrettini beat Nikoloz Basilashvili 6-7 (5-7) 6-2 6-3 to reach the third round, while Diego Schwartzman, Gael Monfils and Lorenzo Sonego moved into the second round.

In the St Petersburg Open, defending champion Andrey Rublev beat Ilya Ivashka 6-4 6-4 to reach the quarter-finals along with Denis Shapovalov, a 2-6 6-3 6-0 winner against Pablo Andujar.

Jan-Lennard Struff also moved into the last eight, with Karen Khachanov and Marin Cilic securing first-round wins.

Stefanos Tsitsipas survived a minor scare in the first round of the Vienna Open before ultimately going on to beat Grigor Dimitrov in straight sets.

It was neck-and-neck for much of the first set, with neither player losing serve, but Dimitrov appeared to have the upper hand when he got to 6-3 in the tiebreak.

Tsitsipas recovered emphatically, however, the top seed reeling off five successive points to win the set and he went on to book his spot in the second round thanks to a 7-6 (8-6) 6-4 victory. He will face Frances Tiafoe next.

"Grigor is a tough competitor and the level of tennis was really high today. We both competed at our highest [level]," Tsitsipas said afterwards.

"That was great tennis that was being played during the entire match and I got really close to my [best] offence and showed incredible attitude [in] the last game, which was the one that was the most crucial of the match."

Alexander Zverev, seeded second, was also made to work in his first-round clash with Filip Krajinovic.

While he blew the Serbian away in the first set, he found himself 5-2 down in the second as Krajinovic looked set to level the match, but Zverev scrapped his way back and then served to love to win 6-2 7-5. Alex de Minaur awaits the German.

Casper Ruud and Felix Auger-Aliassime, seeded fourth and sixth respectively, were two other high-ranking players who also secured progression, boosting their ATP Finals qualification hopes.

Ruud was pushed hard by Lloyd Harris but eventually outfought the South African in his 7-5 7-6 (7-2) win, while Auger-Alisassime made fairly light work of Ricardas Berankis 6-3 6-2.

Indian Wells champion Cameron Norrie, who is also in with a shot of reaching the ATP Finals, beat Marton Fucsovics 7-6 (7-4) 6-1 to set up a meeting with Auger-Aliassime – the British number one is 11th in the FedEx ATP Race to Turin rankings, one above his next opponent.

At the St Petersburg Open, fifth-seed Taylor Fritz was the highest-ranked player in action and he needed a little over an hour to beat Emil Ruusuvuori 6-1 6-4.

Pablo Andujar defeated Federico Delbonis to set up a meeting with second seed Denis Shapovalov, while Ilya Ivashka beat Laslo Djere for the right to tussle with tournament favourite Andrey Rublev next.

Jelena Ostapenko wasted little time in her opening match at the St Petersburg Ladies Trophy, while there were also wins for Aliaksandra Sasnovich and Vera Zvonareva in Monday's action. 

Ostapenko needed less than an hour to get past Paula Badosa, who caused an upset when the pair met at last year's delayed French Open. 

There was to be no Roland Garros repeat for Badosa, though, as she was swept aside 6-2 6-2.  

The sixth-seeded Ostapenko started her campaign impressively in Russia, producing 26 winners and just eight unforced errors. Her serve was also in good order, never giving her opponent a chance of a break. 

Sasnovich had to work a little harder, rallying from a set down to see off Ana Bogdan 2-6 6-2 6-1. Her reward is a clash with third seed Fiona Ferro, who received a bye through to the second round.

Zvonareva, meanwhile, progressed in straight sets against Arina Rodionova, the Russian dropping just four games during a contest that lasted one hour and 22 minutes.  

Victory was sealed at the second opportunity, a sliced backhand into the net by her opponent sending Zvonareva through to the last 32. 

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