Jannik Sinner was a class above on the grass in 2025, leaving many wondering just how many titles he can win at SW19…
Having previously lost in the Wimbledon quarterfinals twice (2022, 2024) and the semifinals once (2023), Sinner was looking to go all the way in 2025.
Reaching the final with wins over the likes of Ben Shelton and Novak Djokovic, Sinner came face-to-face with his greatest rival, Carlos Alcaraz, once more.
Avenging his defeat to the Spaniard in Paris, Sinner fought back from a set down to beat Alcaraz 4-6, 6-4, 6-4, 6-4, clinching his maiden Wimbledon title.
When he returns in 2026, Sinner may well be considered the favorite to defend his title, as the world number one truly looked unbeatable at times during his two-week stint at the All England Club this summer.
However, while he certainly looks to be the best grass-court player alive in 2025, how would he have fared against one of the greatest to ever do it?
Andy Roddick believes ‘prime’ Roger Federer would beat Jannik Sinner on grass
During the latest episode of ‘Served with Andy Roddick’, 2003 US Open champion Andy Roddick was asked who would win in a match between ‘prime’ Roger Federer and 2025 Sinner.
“It’s surface dependent big time,” said Roddick.
“On grass, I think Roger [Federer] has probably the greatest skillset that has ever existed on grass, still in his prime.
“I think I would still take Roger in his prime, but the fact that it is a hard question to answer shows you how good [Jannik] Sinner is and shows you what I think of Sinner.”
Roddick proceeded to explain why Sinner would struggle more against Federer than he has against his fellow ATP Tour stars in 2025.
“What does not exist currently, I think outside of [Carlos] Alcaraz, is that Roger would be able to switch pacing, mix it up, serve and volley, mix his second serve around and put Jannik in different parts of the court,” he said.
“As great as Taylor Fritz is at what he does, Sinner knows what is coming. And if Sinner knows what is coming, it’s like a great hitter in baseball knowing what pitch is coming.
“The variety on the heels of all of these guys being so good from the baseline, being able to take full cuts with luxilon, Daniil Medvedev is a great player and a Hall of Fame player, Sinner knows what is coming in that match-up.
“Against Roger, Sinner would not know what is coming from point to point.
“That’s why Carlos has been so successful in their head-to-head.
| Match | Winner | Loser | Score |
| 2025 Cincinnati Open – F | Carlos Alcaraz | Jannik Sinner | 5-0 (RET) |
| 2025 Wimbledon – F | Jannik Sinner | Carlos Alcaraz | 4-6, 6-4, 6-4, 6-4 |
| 2025 French Open – F | Carlos Alcaraz | Jannik Sinner | 4-6, 6-7, 6-4, 7-6, 7-6 |
| 2025 Italian Open – F | Carlos Alcaraz | Jannik Sinner | 7-6, 6-1 |
| 2024 China Open – F | Carlos Alcaraz | Jannik Sinner | 6-7, 6-4, 7-6 |
| 2024 French Open – SF | Carlos Alcaraz | Jannik Sinner | 2-6, 6-3, 3-6, 6-4, 6-3 |
| 2024 Indian Wells – SF | Carlos Alcaraz | Jannik Sinner | 1-6, 6-3, 6-2 |
| 2023 China Open – SF | Jannik Sinner | Carlos Alcaraz | 7-6, 6-1 |
| 2023 Miami Open – SF | Jannik Sinner | Carlos Alcaraz | 6-7, 6-4, 6-2 |
| 2023 Indian Wells – SF | Carlos Alcaraz | Jannik Sinner | 7-6, 6-3 |
| 2022 US Open – QF | Carlos Alcaraz | Jannik Sinner | 6-3, 6-7, 6-7, 7-5, 6-3 |
| 2022 Croatia Open – F | Jannik Sinner | Carlos Alcaraz | 6-7, 6-1, 6-1 |
| 2022 Wimbledon – 4R | Jannik Sinner | Carlos Alcaraz | 6-1, 6-4, 6-7, 6-3 |
| 2021 Paris Masters – 2R | Carlos Alcaraz | Jannik Sinner | 7-6, 7-5 |
“He can give him a different look, and Jannik does not always know what is coming, so Roger would be able to show him a different look and adjust throughout the match.”
The reality is, we will never know how Sinner would’ve performed against Federer, but it will certainly be interesting to see if he can match his Wimbledon legacy.
How many Wimbledon titles did Roger Federer win?
Making his debut at Wimbledon in 1999, it didn’t take long for the Swiss star to get his hands on the title.
Winning his first Wimbledon title in 2003, Federer added seven more to his trophy cabinet over the next 14 years.
- 2003 Wimbledon – Beat Mark Philippoussis in F
- 2004 Wimbledon – Beat Andy Roddick in F
- 2005 Wimbledon – Beat Andy Roddick in F
- 2006 Wimbledon – Beat Rafael Nadal in F
- 2007 Wimbledon – Beat Rafael Nadal in F
- 2009 Wimbledon – Beat Andy Roddick in F
- 2012 Wimbledon – Beat Andy Murray in F
- 2017 Wimbledon – Beat Marin Cilic in F
Retiring as a record eight-time champion, Federer more than left his mark on Wimbledon’s Centre Court.
Sinner has a long way to go before he reaches those numbers, although if he continues to perform as well as he did in 2025, there’s really no limit to what he can achieve on the grass.
Searching for title number two, Sinner will return to Wimbledon in 2026 when the tournament begins on Monday, June 29.
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