Novak Djokovic reached the Wimbledon quarterfinals for the 16th time but it proved a hard day's work at his Centre Court office as he ground past Australian Alex De Minaur on Monday.
The 38-year-old started abysmally and lost the opening set in 31 minutes but eventually assumed control of a cagey battle to win 1-6 6-4 6-4 6-4 to keep alive his quest for an unprecedented 25th Grand Slam title.
With Roger Federer watching from the front row of the Royal Box, the player whose record eight men's titles Djokovic is trying to equal, the sixth seed's usually surgical game malfunctioned early on as he dropped serve three times.
The hustling and bustling De Minaur continued to cause Djokovic headaches with his shot-placement and movement but the Serb found his range to win the next two sets full of attritional baseline rallies.
Even then Djokovic looked like getting dragged into a fifth set as De Minaur jumped 4-1 ahead in the fourth and had a point for a 5-1 lead, but he slammed the door shut just in time, winning five games in a row to take his place in the last eight where he will face Italian 22nd seed Flavio Cabolli.
Djokovic gets it done 💪
— Wimbledon (@Wimbledon) July 7, 2025
After going a set down against Alex de Minaur, Djokovic recovers to win 1-6, 6-4, 6-4, 6-4 against the Australian and move into his 16th #Wimbledon quarter-finals 😮
There's just no stopping him ⚡️ pic.twitter.com/mIRU2jjkXF
"I don't know how I'm feeling to be honest. I'm still trying to process the whole match and what happened on the court. It wasn't a great start for me, it was a great start for Alex," a weary Djokovic said on court.
"He was just managing the play better from the back of the court and I didn't have many solutions. I was very pleased to hang tough in the right moments and win this one."
Djokovic has now won 43 of his last 45 matches at Wimbledon and not since 2017 has he failed to reach the final.
The two losses were against Carlos Alcaraz in the last two finals, but for half an hour on Monday it looked as though Old Father Time might finally be catching up with him.
FIRST MEETING
Djokovic had never met the man nicknamed 'Demon' on a grass court after last year's quarterfinal between them never happened when the Australian withdrew with a hip injury.
He predicted beforehand that the 26-year-old would be a handful on the surface and he was proved right.
With a relaxed Federer watching in an immaculate blue suit and shades, Djokovic's game crumbled into a heap of double-faults, errant forehands and clumsy footwork.
"Sometimes I wish I had a serve and volley, and a nice touch from the gentleman that's there. That would help," Djokovic said of his old rival after sealing his 101st Wimbledon win in a grinding three hours and 19 minutes.
"It's probably the first time he sees me and I win. The last two I lost. It's good to break the curse."
De Minaur's game plan seemed to be to drag Djokovic into cat and mouse rallies and initially it worked.
But Djokovic rebooted his computer-like brain and chipped away at the Australian who must have believed he could snap his 10-match losing streak against top-10 players.
Djokovic won a 34-stroke rally early in the second set but with service breaks being traded like a plummeting stock and Federer heading off for afternoon tea he simply could not shake off the tenacious De Minaur.
Serving at 5-4, Djokovic had to save two break points before levelling the match. He looked more like his dominant best to control the third set and having not lost a two sets to one lead since 2010 it seemed like victory was a formality.
There was another twist though and it was a mightily relieved Djokovic who closed out the win.
SHELTON GETS ONE UP ON DAD AS HE BATTLES INTO QUARTERS
American 10th seed Ben Shelton reached the quarterfinals for the first time when a 3-6 6-1 7-6 (1) 7-5 victory over Italian Lorenzo Sonego also gave him the family bragging rights.
Thirty-one years ago Shelton’s father and current coach Bryan lost 10-8 in the fifth set to Christian Bergstrom in the last 16 at Wimbledon in what proved the high-point of his Grand Slam career.
Shelton junior, who has previously reached the semis at the Australian and US Opens, was a little ragged as he dropped his first set of the tournament, but the powerful left-hander found his length and attacked the net more in a dominant second set, and then raced through a third-set tie-break.
In a nip and tuck fourth, Shelton, sporting a Rafa Nadal-style sleeveless vest, delivered an athletic final game to break and take the match, roaring in triumph.
His time is now.#Wimbledon | @BenShelton pic.twitter.com/UByYSUmy6o
— Wimbledon (@Wimbledon) July 7, 2025
Shelton, 22, was quick to credit his father, watching from the players' box on Number One Court.
"He kind of inspires the way that I'm playing on grass, the way that I'm moving forward, how I'm cutting off angles, wanting to mix in the serve and volley vintage style of tennis every once in a while," he said.
"He was a serve and volley -- I think I'm better than him from the baseline."
Shelton came into the match having not only not lost a set, but having dropped only two service games in three rounds.
After beating Sonego at the Australian and French Opens this year and with the Italian coming off a marathon five-hour match on Saturday, Shelton must have been in confident mood, but he was somewhat wild in the first set.
Sonego, also seeking a first Wimbledon quarter-final, was unable to maintain his consistency in the second set and Shelton quickly took command with a double break.
It looked like a relatively straightforward third set too as Shelton ramped up the power to grab an early break but Sonego dug in superbly to break back, only to be blown away 7-1 in the tie-break.
Sonego forced a rare break point at 2-2 in the fourth but Shelton somehow scrambled a brilliant John McEnroe-style pick-up half-volley to save it and went on to hold.
They then went toe to toe until the thrilling final game, highlighted by Shelton's fabulous running forehand, after which he leaped a mile off the ground to punch the air in celebration.
Shelton duly completed the win to earn a probable quarterfinal against another Italian, world number one Jannik Sinner, where a victory would make it three years in a row that an American had made the semifinals after Taylor Fritz and Chris Eubanks.
THE SHELTON SCREAM RETURNS 📣
— Wimbledon (@Wimbledon) July 7, 2025
No.10 seed Ben Shelton recovers from going a set down against Lorenzo Sonego to win 3-6, 6-1, 7-6(1), 7-5 and reach his first #Wimbledon quarter-finals ➡️ pic.twitter.com/WOMG4htz52
"It was difficult," Shelton said. "Every time I needed a big point, he comes up with a highlight shot, and maybe the same vice-versa, but it was a lot of fun.
"I'm happy with the way that I played that last game. I felt like that was my best tennis, my best returning, and it's what I'm going to need to continue in this tournament.
"To end the match with that sort of game gives me a lot of confidence."
COBOLLI BRINGS FLAIR AS ITALIAN SURGE GATHERS STEAM
Flavio Cobolli marched into the quarterfinals on, leading a dashing Italian advance by snuffing out the once-lethal Marin Cilic in a statement win that lit up a sunny but breezy Court Two.
Wielding his bright orange racket like a fluorescent sabre, the 23-year-old carved through the Croatian’s defences to win 6-4 6-4 6-7(4) 7-6(3), lighting the way for compatriots Jannik Sinner and Lorenzo Sonego.
'It's a maiden major quarter-final for Flavio Cobolli" 🥹
— Wimbledon (@Wimbledon) July 7, 2025
Italian Cobolli defeats Marin Cilic to reach the Last 8 of #Wimbledon for the first time, doing so by winning 6-4, 6-4, 6-7(4), 7-6(3) 💥
Just look at what it means to him and his family ♥️ pic.twitter.com/LVLb9moNKI
Both hope to follow him through later in the day and set a Wimbledon record of three Italian men into the last eight.
For Cilic, now 36 and a finalist here in 2017, it was a flat, sobering exit — a campaign that had briefly stirred echoes of past glories ending with a performance that just did not show verve or resolve.
Cobolli next will face either Australian Alex de Minaur or tennis titan Novak Djokovic but either way will surely fear nobody after such a confidence-boosting performance.
Compact and bristling with youthful energy, he owned the court during the first two sets, firing groundstrokes fizzing into Cilic’s side throughout, while the big man — a former US Open champion — took bigger strides, made bigger cuts at the ball and was repeatedly forced into bigger errors.
There was less fanfare out on Court Two than on the raucous night Cilic had turned back time to topple fourth seed Jack Draper. And this time the Croatian just failed to spark.
Not so Cobolli.
Buoyed by pockets of vocal Italian support, he quickly got into his groove before showing there is far more to his arsenal than rock-solid groundstrokes — unfurling a series of beautifully deft volleys and feathered drop shots that delighted an increasingly appreciative crowd.
A single break of serve in each of the first two sets put him firmly in the driving seat before Cilic delved deep into his well of wiles and somehow managed to steal the third set on a tiebreak.
Cilic broke again for 4-3 in the fourth set as Cobolli’s frustration started to show and the Croat’s shadow loomed ever larger, but 22nd seed Cobolli kept hammering away and broke back immediately thanks to a backhand winner.
Reprieved, he went on to force a second tiebreak and this time made no mistake, clinching victory when Cilic fired an unforced error — his 64th of the match.
SINNER INTO QUARTERS AFTER INJURED DIMITROV RETIRES
A heartbroken Grigor Dimitrov left Wimbledon's Centre Court in tears after being forced to retire injured when two sets up in his last-16 battle against Jannik Sinner, handing the top seed a remarkable reprieve.
Sinner himself had suffered a nasty fall in the opening game of the fourth-round clash and appeared to be suffering discomfort in his right elbow.
The Italian was unable to cope with Dimitrov's varied style across the opening two sets, and was staring at a shock exit when trailing 3-6, 5-7, 2-2.
Yet the 34-year-old Bulgarian, who has now retired in each of his past five Grand Slam appearances, pulled up holding his right pectoral muscle and was unable to continue.
A sight we never want to see.
— Wimbledon (@Wimbledon) July 7, 2025
Grigor Dimitrov is forced to retire while leading two sets to love. Everyone at #Wimbledon is wishing you a speedy recovery, Grigor 💚💜 pic.twitter.com/qBwiMbq3e2
"Honestly I don't know what to say," said Sinner. "He is an incredible player, I think we all saw this today.
"He's been so unlucky in the past couple of years. An incredible player, a good friend of mine also. We understand each other very well off the court too.
"Seeing him in this position, honestly, if there would be a chance that he could play the next round, he would deserve it."
"I don't take this as a win at all."
— Wimbledon (@Wimbledon) July 7, 2025
Jannik Sinner was full of respect for his friend Grigor Dimitrov after he was forced to retire.#Wimbledon pic.twitter.com/bQTsxUM8Mu
Dimitrov, the 19th seed, served an ace out wide to hold serve for 2-2 in the third set but then collapsed in pain.
Sinner rushed to his aid before Dimitrov went off court, but he returned just moments later in tears and was unable to continue, barely able to wave to acknowledge the crowd's warm ovation.
Jannik Sinner was there for his opponent in a cruel moment on Centre Court#Wimbledon pic.twitter.com/HGIs5yOaD5
— Wimbledon (@Wimbledon) July 7, 2025
"I hope he has a speedy recovery," said Sinner, 23. "It's very unlucky from his side. I don't take this as a win at all. This is just a very unfortunate moment to witness for all of us.
"I think already in the last Grand Slams he has struggled a lot with injuries and seeing him now again having this kind of injury is very, very tough. We all saw this with his reaction, how much he cares about the sport."
Dimitrov's injury woes began 12 months ago at Wimbledon, where he slipped and damaged his knee in the first set of his fourth-round clash against Daniil Medvedev.
He was forced to retire from matches at the US Open, Australian Open and the recent French Open.
Sinner, into the quarterfinals at Wimbledon for the fourth consecutive year, will next face world number 10 Shelton.
He is on a potential semifinal collision course with seven-time champion Djokovic, but there will be question marks over the Italian's own fitness after his struggles against Dimitrov.
Sinner has never reached the Wimbledon final, going as far as the semifinals in 2023.
He has played in the past three Grand Slam finals, taking the title at the US Open and the Australian Open and losing the French Open showpiece in a five-set epic against Carlos Alcaraz in June.