No. 1-seeded Spaniard Carlos Alcaraz will reach the semi-finals for the first time at Wimbledon, where he will face Russia's No. 3-seeded Daniil Medvedev.
Alcaraz beat sixth seed Holger Ron of Denmark 7-6 (7-3), 6-4, 6-4 in the quarterfinals.
The 27-year-old Medvedev went unseeded in a thrilling five-set match to break Chris Eubanks' dream streak.
Medvedev, who had never made it past the 1/8 final, defeated the USA 6-4, 1-6, 4-6, 7-6 (7-4), 6-1.
Alcaraz and Medvedev, who won major hard-court titles at the US Open, will play in the bottom four on Friday and aim to reach the Wimbledon World Cup final.
In the other semifinal match, No. 8 and No. 2 Serbia's Novak Djokovic will face No. 8 Italy's Yannick Sinner.
A dream to reach the semi-finals - Alcaraz
Alcaraz and Loon are regarded as two of the most exciting prospects in men's football, and expectations are high, potentially creating an exciting rivalry in the years to come.
Born just a week after Loon in 2003, Alcaraz is clearly ahead of his growth, having already won the World No. 1 title and his first Grand Slam title.
With a dominating performance in his first ever Wimbledon quarter-final, the stunning Spaniard has proven once again that his time has indeed come here.
It's easy to forget that Alcaraz has just entered his fourth championship on turf, but it's the speed and quality that the Queen's champion has adapted to this summer.
"It's a dream for me to play in the semi-finals here. I think I'm playing well and I'm at a good level. On the surface, it's crazy," he said.
Ron's growth on grass was also fast. Although he hadn't won a professional match on the ground until this summer, he was expected to be able to defeat Alcaraz in the long-awaited showdown.
Ron scored an early break point and Alcaraz saved with a head, but there were few extra chances.
Alcaraz put the pressure on the Dane as he made two attempts to stay in the party, but continued tensions on Center Court prevented him from tying the score.
No one can predict with certainty what path a decision maker will take.
However, Ron's double fault at 3-3 gave the momentum and Alcaraz let out a deep roar as he took control and took the lead with a powerful backhand.
Another close group followed, leaving little choice between the two couples. Another runic mistake turned out to be fatal.
A ball sucked into the net created a break point, causing the fans to roar as Alcaraz fired a brilliant shot down the line from the left.
Ron walked off the court to reset my mind and it seemed to work as he kept the love early in the third set.
But he was given a time violation for taking too long to serve at 2-2, contributing to Alcaraz breaking and the set running away from him.
Alcaraz was unable to take a match point when Rune served at 5-3 but came through a minor wobble in the next game to become the youngest Wimbledon men's semi-finalist since Djokovic in 2007.
"I feel like whoever got that first set had a big advantage," said Rune, who added he did not feel well when he woke up on Wednesday morning.
"I did my best in the circumstances. I fought until the end. He played a good match, I could have played better. It's a part of it and I just have to move on."
Medvedev reaches first Wimbledon semi-final
When Medvedev faces Alcaraz it will be the first time the Russian has featured in a Wimbledon semi-final and the fourth time he has made this stage at a Grand Slam tournament.
With the decision made to keep the roof closed on Court One, a cacophony of noise was generated with the sound of the ball hammering off racquets and cheers from the crowd echoing around the arena.
On his debut in the Wimbledon main draw, big-hitting Eubanks was featuring in a first Grand Slam quarter-final and had the backing of the British crowd.
The world number 43 has endeared himself to the All England Club crowds by bringing his style and personality to the grass courts, despite having claimed it is the "stupidest surface" earlier this summer.
Medvedev took a comfortable first set but Eubanks' powerful shots from the baseline and rapid serving quickly wrapped up the next two to give him the lead.
The Russian stuck to his game plan in the fourth set and relied on the notion that he could maintain his level for the long run.
That plan worked as Eubanks faded away in the deciding set, falling a double-break behind and ultimately succumbing after sending a forehand long.
Medvedev has never lost on Court One and his greater experience in latter stages of tournaments proved too much for the underdog.
But Eubanks will reflect on a stunning grass-court swing, where he won a first ATP title and will rise into the world's top 40 having never previously cracked the top 100 until April.
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