Daniil Medvedev prevailed 6-7 (7-9) 6-4 7-6 (7-4) 2-6 6-3 over world number one Jannik Sinner to reach the semi-finals at Wimbledon.
In a four-hour epic, the Russian outlasted top seed Sinner to reach the last four at the All England Club for a second straight year.
Since 2000, Medvedev is only the fourth player to defeat the men's number one on three or more occasions at grand slams, along with Novak Djokovic, Rafael Nadal and Stanislas Wawrinka.
Sinner, who was forced to take a medical timeout due to illness midway through the third set, rallied brilliantly from that issue in the fourth to force a decider.
However, the Italian ran out of steam in the fifth set, with Medvedev going on to clinch victory with three match points to spare, briskly sending Sinner around the court before drilling a winner down the line.
"I knew if I wanted to beat Jannik it was going to be a tough match, he's not a guy you can beat easily, even if he wasn't feeling that good," said Medvedev.
"I managed to stay at a high level, a great match and I'm really happy with my game looking forward."
Asked what it was like to face Sinner after the medical timeout, Medvedev added: "It's actually very tough. One moment, I could see he wasn't moving well.
"It's tricky because you want to play more points to make him suffer more, but then at the same time, you know he will come back and go full power. In a way, I would prefer not to have this situation."
Medvedev will face either Tommy Paul or reigning champion Carlos Alcaraz in the semi-finals.
Data Debrief: Dragging on...
There have now been 36 five-set matches in the men's singles at Wimbledon this year, surpassing the 1983 US Open and 2024 Australian Open (35 each) for the most at a single grand slam event in the Open Era.
Medvedev, meanwhile, has now reached nine semi-finals at majors, though the 28-year-old has only progressed from two of those previous eight ties.
USVI secures 2-1 win over hosts Trinidad & Tobago in Davis Cup Americas Group IV round robin
The US Virgin Islands secured a 2-1 win over hosts Trinidad & Tobago in Davis Cup Americas Group IV Round Robin play at the National Racquet Centre in Tacarigua on Tuesday.
The hosts got Tuesday’s tie off to a winning start with Kamran McIntosh-Ross securing a dominant 6-0, 7-5 win over Tomas Del Olmo in an hour and 21 minutes.
McIntosh-Ross had an excellent day on serve, winning 80% of his first serve points and saving all three break points faced.
The 20-year-old also was able to break Del Olmo’s serve four times.
Overall, the Trinidadian won 71 points compared to Del Olmo’s 47.
USVI levelled proceedings at 1-1 when Jan Neuburger-Higby beat Luca Shamsi 6-1, 6-2 in just over an hour.
Neuburger-Higby won 79% of his first serve points and converted all four of his break opportunities on Shamsi’s serve on his way to a comfortably victory.
The tie then came down to a doubles match between T&T’s Kale Dalla Costa and Alijah Leslie and USVI’s Del Olmo and Neuburger-Higby which the USVI pair dominated on the way to a 6-2, 6-3 victory.
Murray confirms retirement after Olympics
Andy Murray has confirmed he will retire after the Olympic Games in Paris.
The 37-year-old is set to compete in both the men's singles and doubles at what will be his fifth Olympics.
Murray first competed in Beijing in 2008 and won his first gold medal four years later in London with a straight-sets victory over Roger Federer.
He then became the first male player to win two singles titles at the Games by beating Juan Martin del Potro in Rio in 2016.
In a post on X, Murray wrote: "Arrived in Paris for my last ever tennis tournament.
"Competing for Team GB has been by far the most memorable weeks of my career and I'm extremely proud to get to do it one final time!"
Murray made his final appearance at Wimbledon, where he is a two-time champion, before the Olympics, suffering a first-round defeat with brother Jamie in the doubles.
He later received an emotional tribute on Centre Court to mark his achievements at the tournament.
Zverev confident of retaining Olympic gold despite injury concerns
Alexander Zverev is confident of claiming a second Olympic gold medal at the Paris games despite picking up an injury at Wimbledon earlier this month.
Zverev slipped during his third-round triumph against Cameron Norrie in SW19, bowing out of the competition in a five-set to Taylor Fritz in the following round.
The world number four has since competed in the Hamburg Open, a title he won a year ago, but fell at the final hurdle to Arthur Fils in a decisive final set tie-break.
Zverev, who became the first German to win an Olympic gold medal in singles since Steffi Graf did so in 1988, beat Karen Khachanov in the final in Tokyo four years ago.
The German described his injury as a bone edema and torn capsule and said that it did not require surgery ahead of the games.
"To be honest, you know, the risk will stay for the next two, three, four weeks maybe because that's how long the bone heals, and that's what everybody told me," Zverev said.
"But, at the end of the day I also knew that I don't want to rest for four weeks because, now we're playing on the surface where I don't see that big of a risk of doing the same motion again and doing the same movement again."
The tennis will take place at Roland Garros, a venue well-known to Zverev who reached the French Open final earlier this year, losing out on a first grand slam title to Carlos Alcaraz in five sets.
Zverev is also on the shortlist of German athletes who could be flagbearer for the nation during Friday's opening ceremony.
"If someone told me that I should walk in as a flag bearer, it would mean even more to me, to be honest (than winning the Olympics)," Zverev was quoted by SpilXperten.
"Leading an entire nation and so many top German athletes into the Olympics is simply the greatest honour an athlete can receive.
"And of course, the gold medal I won at the last Olympics is one of the highest achievements you can have in sports and for me personally the greatest success in my career."
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