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Novak Djokovic reached his first ATP semi-final in February 2006 in Zagreb, falling to Ivan Ljubicic in three tight sets.

Novak Djokovic opens up about how Roger Federer 'helped me a lot'

Nearly two decades later, the 38-year-old is still capable of reaching the latter stages on the highest level.

Novak defeated two rivals at this week’s ATP 250 event in Athens, having advanced to his eighth ATP semi-final of the season. Thus, the legend now stands on 199 ATP semi-finals, moving one away from another incredible milestone.

Jimmy Connors and Roger Federer are the only players with 200 ATP semi-finals in the Open era, with Djokovic looking good to join them at the end of 2025 or the beginning of the new season.

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Federer stands on 211, and the Serb will have a chance to pass him if he remains this consistency in 2026 and 2027. Novak has stopped the clock this season after reaching six notable semi-finals.

The Belgrade native made an incredible run at Majors, reaching all four semi-finals and writing history books. Alongside, he also competed in the last four at the Miami Masters and in Shanghai.

Djokovic suffered a couple of early losses, and without them, he could have already been on 200. However, the milestone will come sooner rather than later. Novak skipped the Paris Masters and prepared for the ATP 250 event in Athens.

The veteran defeated Alejandro Tabilo 7-6, 6-1 in the first round, besting the Chilean for the first time in a career after two losses on clay. Djokovic prevailed in the opener after over an hour and secured a double break in the second set to advance.

Novak chased his 199th ATP semi-final against Nuno Borges and delivered a hard-fought 7-6, 6-4 victory. As in the first match, the Serb had to dig deep in the opening set. He played a flawless tie break to gain the advantage.

Novak secured a single break in the second set and served well to book a place in the last four, remaining on the course toward his 101st ATP title.

Why Federer & Zverev’s controversial Carlos Alcaraz & Jannik Sinner theory doesn’t make sense

Roger Federer and Alexander Zverev have sparked debate by expressing a controversial theory they share — involving Carlos Alcaraz and Jannik Sinner — about tennis court speed.

Tennis icon Federer claimed that tournament directors are preparing slower surfaces to favour both Alcaraz and Sinner as they want to see the leading duo meet in finals.

“I understand the safety net that the tournament directors see in making the surface slower,” the 20-time Grand Slam champion said on the Served with Andy Roddick podcast during the Laver Cup.

Why the Carlos Alcaraz, Jannik Sinner conspiracy theory by Federer & Zverev  is wrong

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“It’s for the weaker player — he has to hit extra amazing shots to beat Sinner, whereas if it’s quick, he can only maybe blast a few and, at the right time… and he gets past.

“So that’s what the tournament directors are [thinking], like: ‘I kind of like Sinner-Alcaraz in the finals, you know? It kind of works for the game’.”

The Swiss added: “We need to have not only fast courts, but what we would want to see is Alcaraz or Sinner figure it out on lightning fast, and then have the same match on super slow and see how that matches up.”

Zverev, the current world No 3, criticised the lack of variety in playing surfaces and echoed Federer’s suggestion that this is an intentional strategy that gives Alcaraz and Sinner an advantage.

“I hate when it’s the same, to be honest,” the German said during the Shanghai Masters.

“I think the tournament directors are going towards that direction because, obviously, they want Jannik and Carlos to do well every tournament and that’s what they prefer.

“Nowadays, you can play almost the same way on every surface. I don’t like it, I’m not a fan of it. I think tennis needs different game styles, tennis needs a little bit of variety and I think we’re lacking that right now.”

Federer and Zverev’s points about the homogenisation of court speeds and conditions are certainly valid. Some tennis analysts and fans have long questioned the lack of court diversity in the modern game.

There are now far fewer courts at the extreme ends of the speed spectrum than there were in the 1990s or in earlier eras, when there were much quicker grass and indoor courts (hard and carpet), and also slower clay courts.

The argument that courts are being made slow to benefit Alcaraz and Sinner, however, makes far less sense.

Sinner was asked directly about Federer and Zverev’s comments after his first match at the Shanghai Masters.

“You know, me and Carlos, we don’t make the courts,” said the Italian.

“It’s not our decision. We try to adapt ourself in every situation. I feel like still every week is a bit different.

“I’ve played some great tennis even when it was faster courts. But I’m not making the courts, you know, so I just try to adapt and play my best tennis I can, and that’s it.”

As Sinner alluded to in his answer, he is by no means a slow-court specialist. In fact, Sinner’s record suggests he is actually at his best on quicker surfaces.

While Sinner has won titles on all four current surfaces (grass, clay, outdoor hard and indoor hard), only one of his 22 titles to date has come on clay (at 250 level in Umag in 2022), which is the slowest court surface.

The four-time major winner has secured seven titles on indoor hard courts and two on grass, which are generally the fastest surfaces.

Sinner played arguably the best tennis of his career to date to win the 2024 ATP Finals on a quick indoor hard-court in Turin. He did not lose more than four games in any of his five matches, and this dominant run emphasised how deadly he can be when his serve and baseline aggression are enhanced by quick surfaces.

Alcaraz is a different case, having won 11 of his 24 titles, and two of his six Grand Slams, on clay courts. He has also thrived on the slow hard courts of the Indian Wells Masters, where he has triumphed twice.

For all of his success in slow conditions, though, Alcaraz is remarkably complete, and he has already proven he can win on a range of courts.

At the age of 21, Alcaraz became the youngest man to win titles on all four current surfaces by securing his maiden indoor title at the Rotterdam Open in February.

The Spaniard, who has secured two Wimbledon crowns and two Queen’s Club Championship titles, also holds a staggering 35-4 record on grass. This gives him an 89.7% grass-court win rate, which is the highest any male player holds on the surface in the Open Era.

Sinner and Alcaraz are arguably just as difficult to beat on quicker courts, and whatever the surface, they are simply in a different category to the rest of the tour.

Novak Djokovic continues to redefine longevity in tennis. The 38-year-old passed his first test at the Shanghai Masters after ousting Marin Cilic 7-6, 6-4 in the oldest match in history at this level!

It was Novak’s first Masters 1000 win since turning 38, becoming the eighth-oldest player to celebrate a win at the premium ATP level of competition. More importantly, Djokovic passed Roger Federer, who delivered his last Masters 1000 victory at 38 years and two months.

At 38 years and four months, Novak now trails only a select group of outstanding veterans. If he maintains this pace and extends his career, he should challenge Ivo Karlovic and Jimmy Connors at the top.

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Alongside them, Stan Wawrinka, Feliciano Lopez, Tommy Haas, Richard Gasquet and Gael Monfils remain in front of the 24-time Major winner. Novak remains competitive at Masters 1000 events two decades after debuting at them.

He lost the Miami final in March in two tie breaks, and Shanghai stands as another chance to seek a deep run against the world’s best players. The latest milestone adds another chapter to a career that has stretched across two decades of hard work and dedication.

Eighteen years after lifting his first Masters 1000 trophies, Djokovic proudly stands in the top-5 and chases notable trophies against much younger and fresher opponents.

While struggling against Jannik Sinner and Carlos Alcaraz at Majors, the Serb believes he can still beat them in the less demanding best-of-three format. He is projected to face Sinner in the semi-final in Shanghai, and he would love to embrace another duel against the four-time Major winner.

While he transitions into the later stages of his career, Djokovic remains competitive on the sport’s biggest stages, mixing endurance and professionalism that few have ever matched.

Novak is facing Yannick Hanfmann in the third round in Shanghai, hoping for another strong performance in his first Masters 1000 event after turning 38.

Roger Federer has revealed details behind the agonising decision he was forced to make over ending his tennis career, with details of the long-running battle he had with knee and back problems highlighting the scale of the challenges he was facing.

Appearing on the Served podcast with his old rival Andy Roddick, the Swiss maestro opened up on the extent of his physical issues like never before, as it was revealed he was using crutches to get around when his knee problem became chronic a year before his retirement.

“I know that your knee went bad, worse, really bad,” said Roddick. “When I saw you in Boston on 2021, the year before you retired, you were hiding your crutches to take photos. Your knee was terrible.”

Roger Federer

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Federer responded with a chuckle, as he said: “Those crutches do not need to be in the pictures!”

Famously, Federer never retired from a match in a career that saw him win 20 Grand Slam titles and he revealed he was hiding the extent of his knee problems in the final phases of his career, as he reflected that his great rival Rafael Nadal took a different approach.

“I was always famous for never being injured,” continued Federer. “I dealt with some back issues, hand stuff, foot things, but never to the extent like it was with the knee at the end.

“It’s only once you’ve had surgery or you are out for a period of time that you are appreciative of how good you used to feel. All of sudden, you are thinking everything through in every moment of the match.

“I didn’t want my opponent or the press to know about my injuries. To protect myself and then on the other side, Rafa was so honest about his issues and I was asking… why is he saying all of that? Me, I can’t get out of the chair with my bad back and everyone thinks I’m perfect.

“I was tricky navigating the media, as I was at 80 per cent and they judged me at 100 per-cent. Look, I had an amazing career with a good and body, but it all came together in the end with the knee.”

Federer went on to reflect on his final match at the 2022 Laver Cup, as he played doubles alongside Nadal before an emotional on-court farewell.

“I felt relief in many ways, because the uncertainty was over,” he said.

“You live with this hope that maybe, just maybe, your body will cooperate again. But once I accepted it, the ending was beautiful.

“Sharing that with Rafa was not planned years in advance; it just happened that way. And I think that made it even more authentic.

“It felt like a perfect ending, considering all the history, all the times I played against Rafa, that he could be next to me,” he told Andy Roddick during a live edition of Served at the Laver Cup.

“When I realised I wasn’t coming back, it was emotional but also peaceful.

“I could share that moment with my team, my rivals, my family, and the fans.”

Roger Federer has floated the enticing prospect of a revival of his iconic rivalry with Rafael Nadal, in comments that will excite millions of tennis fans around the world.

While Carlos Alcaraz and Jannik Sinner’s exciting new rivalry has filled much of the void left behind following the retirements of Federer and Nadal, many tennis fans will always regard the battles between the Swiss maestro and his Spanish rival to be the best in tennis history.

So the prospect of seeing the duo back on court in the near future will set pulses racing and Federer has revealed in an interview with CNBC that he would be open to the prospect of returning to tennis for a seniors tour that could also feature Nadal.

Rafael Nadal and Roger Federer

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When asked whether he would be open to leading a new tour that could feature the icons of tennis, Federer was quick to offer a positive response.

“Yeah, why not?” he said. “I love Rafa. I played four hours of tennis here in San Francisco and also an hour and a half in LA. I am playing a lot, I’m trying to keep in good shape.

“I know Rafa is open to playing some more tennis. It sounds terrible… seniors tennis. Maybe we can create a tour. A ‘Fedal’ Tour.

“One of the reasons I started the Laver Cup was to shine a light on the past greats of the game and maybe a seniors tour, we’ve had it in the past.

“There is a lot of appetite to see past champions in tennis, so I could look into that, for sure.”

Federer spoke about life after tennis earlier this year, as he admitted he needed some time to adjust to his new life after he hung up his rackets following a doubles match alongside Nadal at the 2022 Laver Cup in London.

“I didn’t have any plans per se as I was always trying to come back and then all of a sudden I realised that was it,” Federer told the ATP.

“And then I was just ‘okay, it is over, what now?’ I think now I feel I am more in control of my schedule as before I was just… the afterburn of having just retired, so it has been good, honestly.

“I have to be careful I don’t do too many things, but at the same time I’m really happy to be busy, I like being with other people, love being with my family, I love to travel. But I guess sometimes you just have to make sure to find the right balance and I feel like I have that, so it’s great.”

“I am trying to go to the gym four times a week and I can’t believe I am actually doing that. I rent the space at home and put the machines in and I got it the week after the Laver Cup in London, so it was like, after my career I finally had a gym.

“A little bit weird once I had retired, so now I have to use it, so I do that well, and I don’t play so much tennis anymore so I have to be a little bit more careful with what I eat and stuff.

“I would still like to play some exhibitions down the road so I want to stay in shape and try to look good a little bit.”

Federer and Nadal may have hit their final balls in anger as professional players, but we might not have seen the last of their great rivalry after all.