The fifth-ranked Medvedev triumphed 6-7 (7/9), 6-4, 7-6 (7/4), 2-6, 6-3 to avenge his Australian Open final loss to Sinner in January.
His four-hour victory also ended a five-match losing streak against the Italian as Medvedev reached his ninth Grand Slam semi-final.
The 28-year-old former US Open winner will face defending champion Carlos Alcaraz who beat Tommy Paul of the United States for a place in Sunday’s final.
The Spanish world number three, seeking a fourth Grand Slam title, beat his 12th-seeded opponent 5-7, 6-4, 6-2, 6-2 under the No. 1 Court roof.
Sinner, a semi-finalist in 2023, on Tuesday required medical treatment early in the third set as he appeared dazed and unsteady on his feet.
He had his blood pressure taken before undergoing a medical time-out.
“I knew if I wanted to beat Jannik it needs to be a tough match. He’s not a guy you can beat easy anymore,” said Medvedev.
“I felt at one moment he was not feeling that good but he started feeling better so I’m happy I managed to still stay at a high level.
“It’s always tricky because you want to play more points to make him suffer a little bit more but in a good way.”
In a tight first set in which neither man gave up a break point, Medvedev edged ahead in the tie-break on the back of a lung-busting 33-shot rally.
However, he squandered a set point and his game suddenly fell apart, serving up a double fault as Sinner pocketed the opener.
The mercurial Russian levelled the quarter-final before Sinner summoned the tournament physio after falling a break down in the third set.
After a 10-minute delay, the 22-year-old resumed play and thrilled the Centre Court crowd when he bravely clawed his way back to 5-5.
He then wasted two set points which allowed Medvedev to sweep through the tie-break.
However, the Italian was undaunted and levelled the quarter-final before Medvedev finished the fresher of the two players, breaking in the fourth game of the final set on his way to victory.
Defending champion Alcaraz on Tuesday shrugged off the loss of the first set to beat Paul and set up a repeat Wimbledon semi-final with Medvedev.
The Spanish world number three, seeking a fourth Grand Slam title, beat his 12th-seeded opponent 5-7, 6-4, 6-2, 6-2 under the No 1 Court roof.
Alcaraz was slow out of the blocks, broken twice by the in-form American in a 72-minute first set.
Paul raced into a two-game lead in the second set as Alcaraz again faltered on serve but the Spaniard got back on level terms and broke again to level the match.
Three breaks in the third set put the world number three in charge and he stepped up another gear in the fourth set, winning 92 percent of first-serve points and making just four unforced errors.
‘Tough start to quarter-final’Alcaraz, seeking to become just the sixth man to capture the French Open and Wimbledon titles back to back, said it had been a tough start to his quarter-final against the recent champion at Queen’s.
“If I’m struggling a little bit to find the solutions, if the opponent is playing great tennis and I don’t get him in trouble, I believe at the end that I’ll be able to come back and be able to find solutions,” he said.
Looking forward to his match against Russian fifth-seed Medvedev, whom he beat last year on his way to winning his first Wimbledon title, he said: “Hopefully I’m going to get the same result.
“He just won against Jannik Sinner, the best player right now, so I know that he’s in really good shape so I have to play my best, I have to believe in myself and try to keep going if I want to beat him.”
Vekic reaches last-fourSun went down 5-7, 6-4, 6-1 as Vekic reached the last four of a Grand Slam for the first time at the 43rd attempt and after 12 years on tour.
“I felt like I was dying out there in the first two sets but I just kept going, hoping to have a chance and it came in the end,” said 28-year-old Vekic.
Sun, ranked 123rd in the world, was playing her eighth match of the tournament, including qualifying, in two weeks and the strain eventually told.
“She played well. Maybe if I could have moved faster, maybe if I didn’t have the cramps, who knows what would have happened,” said Sun, who will rise into the top 60 thanks to her All England Club run.
Vekic will face Italian seventh seed Jasmine Paolini who beat 17th-ranked Emma Navarro.
Paolini blazed past American Navarro 6-2 6-1, becoming the first Italian woman to make the Wimbledon semi-finals.
The 28-year-old’s victory ensured she eclipsed compatriots Camila Giorgi (2018), Francesca Schiavone (2009), Silvia Farina Elia (2003) and Laura Golarsa (1989), who had all reached the quarter-finals at the grasscourt Grand Slam in the Open era.
“It’s unbelievable, it’s amazing to get the win in this special court. I’m so happy to be in the semi-final. I don’t know what to say in this moment,” a grinning Paolini said.
“It’s a dream to be here in this position... I was watching finals when I was a kid, on this court.
“I have to say today I played a really good match, she’s a really tough opponent, I lost (to) her three times in the last year, so it was tough.”
“In the semi-finals you have to play tough opponents, and she’s playing amazing,” Paolini said.
“I hope to enjoy the next match, to give 100% and I’m going to fight on every ball. I’m just so grateful to be here another time, in front of you guys.”
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