By securing the win over Ofner in the Round of 64, Sinner has officially matched Federer’s mark of 29 consecutive victories in Masters 1000 events. He will have the opportunity to surpass the Swiss legend on Monday, May 11, when he faces the winner of the match between Alexei Popyrin and Jakub Mensik.

Currently, Novak Djokovic holds the absolute historical record for the longest Masters winning streak, having secured 31 consecutive wins in 2011 and another 30 between 2014 and 2015. If Sinner reaches the semifinals in Rome, he could potentially stand alone at the top of that list.

Sinner aims for the Career Golden Masters

The Italian is on the verge of rewriting tennis history in the Eternal City. Beyond the winning streak, Sinner is chasing a milestone that would see him join the most elite company in the sport’s history. Should he claim the trophy this week, Sinner would achieve the Career Golden Masters—winning all nine ATP Masters 1000 tournaments at least once.

To date, Djokovic is the only player to have achieved this feat, doing so twice. The 24-time Grand Slam champion first completed the set in 2018 at Cincinnati and repeated the achievement at the same venue in 2020.

Ending a national drought

Sinner also carries the hopes of the home crowd as he looks to make Italian history. If he captures the title, he will become the first Italian man to win in Rome since Adriano Panatta in 1976, ending a half-century wait for a homegrown champion at the Foro Italico.

By defeating Cobolli, Zverev became only the fourth man to reach the semifinals at each of the first four Masters 1000 events of the season (Indian Wells, Miami, Monte-Carlo, and Madrid) since the series began in 1990. He joins an elite list featuring Federer (2006), Nadal (2010, 2011), and Sinner (2026). “It’s amazing but, of course, I need to get past this stage now,” Zverev said with a smile during his on-court interview.

While he reached the semifinals in the three previous Masters events this year, he fell to Sinner on all three occasions. Fortunately for the German, the World No.1 is on the opposite side of the bracket this time; Zverev will face Alexander Blockx, who is coming off an upset win over reigning champion Casper Ruud.

Zverev gets redemption against Cobolli

The victory was particularly sweet as it came just two weeks after Cobolli defeated Zverev in the Munich Open final (6-3, 6-3). While the loss in Munich cost Zverev a title on home soil, the story was different in Madrid.

“No revenge. I love Flavio. He’s one of my favorite guys on Tour,” Zverev told the ATP Tour website. “I have a great relationship with him and a great relationship with his father. This is sport… Sports can change very quickly. In Munich, he played an amazing match and I didn’t play a very good match. Today, it was maybe the opposite”.

A new German milestone on clay

Beyond the tournament bracket, the win was historic for German tennis. With his victory over Cobolli, Zverev now records 179 career wins on clay. This breaks his tie with Philipp Kohlschreiber (178), making Zverev the German player with the most wins on this surface in the Open Era.

By reaching the final four in Madrid, Sinner has now reached the semifinals of all nine Masters 1000 tournaments. He becomes only the sixth player to complete the semifinal set, joining Nadal, Djokovic, Federer, Andy Murray, and Alexander Zverev.

Furthermore, Sinner has reached the semifinals of the first four Masters 1000 events of the season (Indian Wells, Miami, Monte-Carlo, and Madrid). He joins Federer (2006) and Nadal (2010, 2011) as the only players to achieve this feat while ranked World No. 1.

Sinner chasing the Career Golden Masters

Sinner is currently enjoying a dominant season, having swept all four Masters 1000 titles so far in 2026. He is now on a collision course with history as he seeks the Career Golden Masters—winning all nine Masters 1000 tournaments at least once.

If Sinner triumphs in Madrid and follows it up with a win at the upcoming Rome Masters, he will complete the collection. Currently, Novak Djokovic is the only player in the Open Era to achieve this feat, completing it in 2018 and incredibly repeating the cycle in 2020.

Sinner praises rising star Jodar

The Italian faced a stern test against the 19-year-old local favorite. Jodar’s incredible run in Madrid included his first Top 10 win over Alex de Minaur and a victory over Joao Fonseca. While Sinner cruised through the first set, Jodar pushed the second to a tiebreak. However, Sinner’s experience shone through as he swept the breaker 7-0.

“He pushed me to the limit,” Sinner said of Jodar in his post-match interview. “He’s an incredible player. I tried to be ready as much as I could. I’m incredibly happy; it was a very high-quality match. I got a bit lucky in the second set, but also had a bit of experience. I’m obviously very happy to be in the semis here for the first time. It means a lot to me”.

Reaching the mark in just 367 matches (300-67), Alcaraz now sits tied with John McEnroe as the third-fastest player in the Open Era to achieve the feat. By comparison, Nadal required 373 matches to reach 300 wins, while Djokovic took 389 and Federer 423.

Alcaraz’s rapid ascent is a testament to his immediate impact on the tour. While Federer and Djokovic faced steeper learning curves in their early twenties, Alcaraz has maintained an elite win percentage since his debut.

At just 22 years old, the Spaniard has already captured 7 Grand Slam titles—including his historic 2026 Australian Open win that completed his Career Grand Slam—and 19 additional ATP trophies.

Which two players reached 300 wins quicker than Alcaraz?

Despite the Spaniard’s surprising statistics, there are two players who achieved 300 career wins faster than Alcaraz. Jimmy Connors did it in 363 matches, while the legendary Rod Laver achieved it in 355, making him nearly impossible to surpass.

What about Sinner?

Alcaraz’s biggest competition on the ATP Tour today is World No. 2 Jannik Sinner, with whom he has already played seven finals, including three Grand Slams in 2025. However, the Spaniard outpaces the Italian in the race to 300 wins, as Sinner took 381 matches to reach the milestone.

The Monte-Carlo Masters is slowly preparing to host another final between the two stars after both players cleared their quarterfinal hurdles. Sinner will now face Alexander Zverev in the semifinals, while Alcaraz will take on the winner of the match between Valentin Vacherot and Alex de Minaur.

By taking down the Canadian, Sinner extended his winning streak to 20 consecutive matches at the ATP Masters 1000 level. He becomes just the fourth player in the history of the series (dating back to 1990) to reach that mark, joining the legendary “Big Three” of Djokovic, Federer and Nadal.

The World No. 2 will now face Alexander Zverev in the semifinals after the German dispatched rising star Joao Fonseca. Sinner remains focused on his first title in Monaco as he pursues another record held by Djokovic: becoming only the second player to win the Miami Open and Monte-Carlo Masters back-to-back.

Sinner finds rhythm after set streak ends

The five-time Grand Slam champion entered the quarterfinals boasting a dominant run of 18 consecutive Masters 1000 match wins without dropping a single set.

While his streak of 37 consecutive sets won finally ended in a second-set tiebreak against Tomas Machac in the previous round, Sinner noted that his performance against Auger-Aliassime was a significant step forward in form.

“I feel like it was a step forwards today,” Sinner said during his post-match interview. “It was a very tough match. I knew I had to get better in certain areas. The serve is not there yet, where I would love it [to be], but all things considered I’m very happy. Yesterday I was very tired. I recovered very well… Let’s see what’s coming tomorrow, but in any case, very happy to be back in the semis”.

When is Sinner playing vs Zverev?

With the semifinal bracket nearly set, Sinner is scheduled to face Zverev on Saturday, April 11. On the other side of the draw, Carlos Alcaraz advanced by defeating Alexander Bublik and awaits the winner of the match between local Valentin Vacherot and Alex de Minaur.

Ahead of the start of the 2026 Australian Open, Federer spoke with ESPN, indicating that he will be following Lionel Messi’s journey closely. The Swiss maestro expressed his hope that the Argentine captain can achieve the fairytale ending he desires for his career—by lifting the trophy once again. “I’ll definitely be following him… Switzerland has also qualified, so I might go. I hope Messi gets the ending he wants for his career,” Federer told ESPN.

The 20-time Grand Slam champion also revealed his deep admiration for Messi as a primary reason for his support in the upcoming World Cup. “He’s done incredible things in soccer, and I’m a big fan of him,” Federer said. “The way he dominated and changed the game is amazing”.

Defending the title won at Qatar 2022 will be Messi’s ultimate goal this year with Argentina, as this is widely expected to be his final appearance for the national team in a World Cup. Both he and Cristiano Ronaldo are set to reach a historic milestone this summer, becoming the first players to ever participate in six different World Cups.

Relief after Qatar 2022

The 2022 World Cup in Qatar remains a defining moment in Messi’s life, as it was the year the Argentine finally secured the world title after the heartbreak of the 2014 final loss to Germany. However, it wasn’t just Argentina celebrating; fans worldwide were rooting for Messi to finally lift the trophy.

Federer was among those supporters who celebrated Messi finally capturing the title that had eluded him for his entire career. Nevertheless, the Swiss legend noted that while the 2022 victory was a massive weight off his shoulders, it doesn’t eliminate the immense pressure that comes with representing a nation on the world stage.

“I’m happy that he’s already won a World Cup, so he won’t have that pressure next time,” Federer added. “Although there’s always huge pressure when you play a World Cup”.

Argentina and Messi will officially begin their title defense in Group J alongisde Algeria, Austria and Jordania. On paper, the Albiceleste are heavy favorites to advance, but as Federer hinted, the pressure of being the defending champions is unique.

It is clear that all three would have been great champions, but the reality is that they constantly pushed each other to the limit in their quest to win, making them lethal competitors. This competitive pressure is easy to understand when one considers that before the Big Three’s emergence, the all-time leader in Grand Slam titles was Pete Sampras with 14 crowns.

Djokovic currently holds 24 Majors and, in the final stretch of his career, dreams of reaching number 25. Rafael Nadal retired in 2024 with 22 Majors, and Roger Federer did the same in 2022 with 20 Grand Slam titles.

On the court, they were massive rivals who competed for absolutely everything, but the relationship among the three was fundamentally based on respect, which remains one of the great legacies these legends left, alongside their immense title haul.

“I feel happy to have been able to be part of this history. Without taking any merit away from Sinner and Alcaraz, who want to do things well, I think we have contributed to new generations being able to think that one can be a fierce competitor without needing to hate the rival. You can have a relationship that is not one of friendship, but excellent. It is a good legacy that we leave in an era of maximum competition,” Nadal emphasized during an interview with Jorge Valdano on Universo Valdano.

Nadal on his relationship with Djokovic and Federer

There is no doubt that the rivalry among the members of the Big Three is the greatest in tennis history, as all three players mutually helped each other reach the supreme level they displayed on the court.

Nadal explained that initially, the competition among the three was lived more intensely, but that things softened over the years as they all matured, leading to a healthy rivalry.

“I believe you go through phases; in the end, when you are younger, you live everything in a much more intense way. Then with the years, things soften, we all grow up, and I believe the positive thing about our era is that we have ended our careers and we can go out to dinner together without any problem, and I think that is something to be proud of,” explained the 14-time Roland Garros champion.

“In the end, we have been competing at the highest level, for the most important things you can compete for in our sport, and aside from the very marked rivalries, we have not taken them to the extreme. I believe the rivalries stayed on the court and the personal relationships were always of respect, admiration, and I believe even a certain friendship toward the rivals,” he concluded.

The Cyprus native became the first player from his country to reach a Grand Slam final, achieving the feat at the 2006 Australian Open, where he fell to Roger Federer. He also rose into the Top 10, reaching a career-high ranking of World No. 8 in August 2006.

Speaking with Tennis365, Marcos Baghdatis chose the most difficult rival of his career: “I would pick Novak Djokovic, simply because I never beat him, but it is very difficult to choose. And I don’t say the Big Three were the only toughest opponents, but there were many others,” he explained.

“That generation of Andy Murray, Rafa, Roger, Novak… of course, those were the four best players who dominated the sport for many years in which I played, but behind them, there were players like Juan Martin del Potro, Stan Wawrinka, Marin Cilic, David Ferrer, Jo-Wilfried Tsonga, Tomas Berdych, and many other players, I think, of a very high level,” the Cypriot, who won four ATP titles, added.

What sets Djokovic apart from Nadal and Federer

Marcos Baghdatis has a long history of facing the members of the Big Three. The Cypriot played Rafael Nadal ten times, only achieving a single victory while he faced Roger Federer in eight opportunities, recording also one win.

However, against Novak Djokovic, they faced each other eight times, and Baghdatis couldn’t secure a single victory. During the interview, he explained that, unlike Nadal and Federer, after a massive loss against Djokovic, he felt that he could never beat the Serbian throughout his career. And that is exactly what happened.

“Whenever I played against Novak, the matches were very even. That is my opinion. Perhaps I am wrong, but what do I remember? Once he gave me a good beating, and that was at Indian Wells. It was a 6-1, 6-3. I left the court and felt like he had given me a lesson. I never felt that way with any other player,” Baghdatis said.

“I never felt that way with Roger or Rafa, even when I was younger and played against Roger, I always thought: ‘Next time I can beat him.’ I always felt that, but with Novak, I didn’t have that feeling, especially after that match,” he concluded.

The Serbian’s most recent title came in Athens, following a three-set victory over Italy’s Lorenzo Musetti in the final. After the win, he granted an interview to Piers Morgan where he reflected on the never-ending debate over the greatest tennis player in history.

“I’ve been asked this a lot over the last few years. Obviously, there are many statistics and people compare them to those of Rafael Nadal and Roger Federer. But I’m going to say what I always say: I’m not going to give my opinion on this topic because I am not in a position to say it,” the Serbian star began.

Djokovic explained his reasoning, citing respect for his competition and the game’s history. “I think it would be very disrespectful to the players who have played against me, such as Nadal or Federer. Furthermore, I don’t feel comfortable talking about it. I consider myself a great student of tennis and I have a lot of respect for all the previous eras,” the all-time men’s Grand Slam champion (24 titles) added.

He concluded by stressing the difficulty of comparing athletes across different generations: “It is very difficult to compare eras, because our sport has gone through many changes in the last fifty years, in terms of technology, equipment, balls, surfaces. Everything has become professionalized, although that doesn’t mean it wasn’t professional before”.

Djokovic impressed with Sinner and Alcaraz

In a major concession, Novak Djokovic expressed doubt about his ability to conquer his 25th Grand Slam title with Jannik Sinner and Carlos Alcaraz currently competing at their peak. The Serbian has now closed the second consecutive year without winning at least one of the four major championships.

“I have been the dominant tennis player for most of my career, and now I am being dominated by Alcaraz and Sinner,” the Serbian noted. “I am aware that, right now, those two are better than me. That is the reality”.

The last eight Grand Slam titles have been split between the Spanish and Italian stars. This means that over the last two years, Sinner and Alcaraz have been the sole champions at the Australian Open, Roland Garros, Wimbledon, and the US Open, clearly illustrating their current dominance over the rest of the tour.

“After retirement I did a lot of rehab. So it wasn’t as if I’d been doing a lot of sports and then suddenly stopped completely. I continued training. But I stopped playing tennis to protect my knee. I did Pilates and tried golf. Surprisingly, I had no pain there” Federer explained in an interview with Tages Anzeiger.

“…My knee feels better. I’m playing much more tennis again now. In the summer I played occasionally with Ivo Heuberger (a former Swiss pro player). Because my children are playing more often and better now, I join them from time to time, too,” he added.

The player who holds the record for the most consecutive weeks at World No. 1 in ATP history, who was recently confirmed for induction into the International Tennis Hall of Fame, also revealed that this physical re-engagement with the sport could lead to major news next year.

“My goal is still to be able to play a few exhibitions again. Maybe something will happen in 2026. I’m now doing a mini build-up until the end of the year,” he said, generating immense expectation.

Nadal, Djokovic, and an eternal bond

Roger Federer also reflected on how a great sporting rivalry, like the one he sustained with Rafael Nadal and Novak Djokovic, ultimately creates a bond that transcends its own time and becomes an important part of history.

“Rivalries like that create a huge bond. I see it very differently today than before, with much more distance. Novak doesn’t know what that’s like yet. Rafa is slowly getting there. When you’re still playing, you can’t think about it the way I do today,” Federe explained.

“The more time passes, the less you identify yourself as an individual player and the more you see the big picture. What’s funny is: Someone might have taken something totally personally—and you can’t even remember it anymore. I’m definitely up for sitting down together and talking about the good old days,” he noted.

Federer elected to the International Tennis Hall Of Fame

It was only a matter of time before the player who held the World No. 1 ranking for the most consecutive weeks in history (310 weeks) was chosen for the International Tennis Hall of Fame. The announcement was officially made, and he will be formally inducted during the ceremony celebrated in Newport from August 27th to 29th, 2026.

“It’s a tremendous honor to be inducted into the International Tennis Hall of Fame and to stand alongside so many of the game’s great champions,” Federer said, according to the ATP official website. “…I look forward to visiting Newport next August to celebrate this special moment with the tennis community“.

This marks the second time Alcaraz has finished as the year-end No. 1, having previously claimed that title back in 2022. In doing so, he became just the second player in ATP history to secure multiple year-end No. 1 rankings before turning 23, joining only Lleyton Hewitt (2001-02).

Although Djokovic holds the overall record for most times finishing the year in the top spot (eight different occasions), while Federer and Nadal did so five times each, none of them managed to do it multiple times before reaching the age of 23, as Alcaraz has now done.

Alcaraz entered the ATP Finals with a 1,050-point advantage over Sinner. The Spanish player did not squander that lead, ensuring he finished the year as the No. 1 ranked player to close out 2025.

After defeating Alex de Minaur and Taylor Fritz in his first two group stage matches, his final victory against Lorenzo Musetti served to secure the No. 1 ranking through the start of 2026. The Spaniard will now face Felix Auger-Aliassime in the semifinals, after the Canadian defeated Alexander Zverev.

Alcaraz on finishing as No.1

One of the conditions for Alcaraz to reclaim the World No. 1 ranking was to win all three matches in the group stage. After defeating Musetti, the Spaniard achieved this objective and secured the top spot to close 2025.

“The match was really important for me, playing for year-end No 1. It means the world to me, to be honest,” Alcaraz said, via the ATP official website. “The year-end No 1 is always a goal. At the beginning of the year, I saw the No 1 really, really far away [with] Jannik winning almost every tournament he plays”.

“But from the middle of the season ’til now, I gave myself the goal for the No 1 because I thought it was there. I had the chance to play great tennis in a lot of tournaments in a row to put myself in with a chance to be close to Jannik for the No 1. Then in the last three, four tournaments of the year, [I was] fighting toe to toe with Jannik for this spot and then finally I got it. For me, it means everything,” the Spaniard added.

Sinner praises Alcaraz’s achievement

In contrast, the Italian missed the chance to finish as World No. 1 for the second time in his career, having finished 2024 in the top spot. However, Sinner acknowledged that Alcaraz fully deserves this achievement after having an exceptional season.

“I’m happy for him, but if I told you I was super happy… I’d be telling a lie! But he deserves it, he’s had an incredible season: he’s won two Slams, eight tournaments. He’s playing at a very high level, he’s competitive on any surface,” Sinner said about Alcaraz.

“He had the pressure too, he managed it very well, but I’m glad for him. He’s a really good guy, he has a great team around him and he’s earned these achievements. For me, this is motivation for next year. If another player were to end up No 1, I’d always choose him — he deserves it,” he concluded.