Daniil Medvedev and Stefanos Tsitsipas suffered surprise fourth-round exits on a day of shocks in the men’s draw at the French Open.

Fourth seed Tsitsipas lost in four sets as teenager Holger Rune reached a maiden Grand Slam quarter-final.

The Dane, 19, punished a lacklustre display from the 2021 Roland Garros runner-up to triumph 7-5 3-6 6-3 6-4.

Rune meets Casper Ruud in the last eight after the Norwegian also won in four sets, beating Poland’s Hubert Hurkacz.

Cilic, 33, next faces seventh seed Andrey Rublev, who progressed to the quarter-finals after Jannik Sinner retired while trailing 1-6 6-4 2-0.

Former US Open champion Cilic, who triumphed at Flushing Meadows in 2014, rolled back the years, taking just an hour and 47 minutes to stun second seed Medvedev under the lights on Court Philippe-Chatrier.

He won 90% of points on his dominant first serve and did not face a single break point, while the Russian’s serve, in contrast, was breached five times.

“It was one of the best matches of my career from start to finish,” Cilic said in his on-court interview. “An absolutely fantastic match from the first point to the last.

“When I’m playing my best tennis, everything is working, serve, return, movement and these last 15 days have been great for me, with some very consistent tennis.

“Against guys like Daniil you have to be able to sustain levels like that throughout the match so I was definitely focused to keep going and I am extremely pleased.

“I try to always give my best even if it’s not going my way. If you are persistent with your training, good things come your way and it is such a pleasure to be playing like this.”

Medvedev’s departure leaves 20th seed Cilic as the only Grand Slam winner remaining in the bottom half of the draw – with Rublev, Ruud and Rune having never previously reached a semi-final at a major.

Rune’s remarkable run continues at Tsitsipas’ expense

Rune had never won a Grand Slam match before this event but has dropped just one set in reaching the quarter-finals.

World number four Tsitsipas seemed strangely subdued for large parts of their fourth-round match, although he levelled after losing the first set and threatened a fightback towards the end of the fourth.

But Rune saved three break points to serve out the match and become the first Danish man to reach a quarter-final on the Paris clay – and the first since 1967 to make the last eight in any Grand Slam.

“I was very nervous, but at the same time I knew that if I went away from my tactics I would lose for sure,” world number 40 Rune said in his on-court interview.

“It was part of the tactic to be as aggressive as possible – Tsitsipas attacks every ball so I had to be aggressive, play fast and I really like playing the drop shots. It worked out and I’m really happy.”

With fellow 19-year-old Carlos Alcaraz also through, it ensured two teenagers are in the last eight of a Grand Slam for the first time since the 1994 French Open.

Rune, who won the boys’ title at Roland Garros in 2019, appeared much fresher throughout, with Tsitsipas perhaps feeling the effects of his two draining opening matches.

The Greek, 23, came from two sets down to beat Lorenzo Musetti in the first round and then took four hours to see off Czech qualifier Zdenek Kolar in round two.

Tsitsipas, however, suggested an equipment change played a part in his below-par display, although he refused to elaborate when pressed on the subject by reporters.

“I wouldn’t put all of the blame on the equipment because it’s something that I chose for my personal progress and getting better,” he said.

“But it kind of stays back in your head that maybe I shouldn’t have done that.”

Ruud sets up all-Scandinavian affair but Sinner bows out

Eighth seed Ruud also made history by becoming the first Norwegian man to reach a Grand Slam quarter-final with his 6-2 6-3 3-6 6-3 victory over Hurkacz.

The 23-year-old’s previous best run at a major came in reaching the 2021 Australian Open fourth round but he assumed control from the off against the Polish 12th seed.

Hurkacz had not dropped serve all tournament but Ruud put paid to that statistic in his very first return game and went on to break on five further occasions.

“It’s been a goal of mine to reach the quarter-finals of a Grand Slam – I feel more experienced now playing a best of five sets,” said Ruud.

Seventh seed Rublev, meanwhile, was the beneficiary of Sinner’s misfortune as the Italian retired in their encounter after the second game of the third set.

Sinner had played his previous matches with heavy strapping on his left knee, but showed few ill-effects as he whizzed through the opening set 6-1 in just half an hour.

However, the 20-year-old required treatment on his knee in the second set as a battling Rublev took it 6-4 to level the match.

Sinner, the 11th seed, was unable to continue after seeing his serve broken early in the third set.