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Kevin Anderson picks who was toughest to face out of Roger Federer, Rafael Nadal and Novak Djokovic

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Novak Djokovic, Rafael Nadal and Roger Federer are undoubtedly the three greatest male players in tennis history.

The trio, who share 66 Grand Slam titles between them, battled against each other for the best part of 20 years on the ATP Tour.

With 24 major titles to his name, Djokovic is considered by many to be the greatest of the three.

Have we seen the last of Novak Djokovic at Roland Garros? 😢

(Getty Images)

However, many consider Roger Federer or Rafael Nadal to be the greatest, pointing to Federer’s Wimbledon dominance and Nadal’s unbelievable record at Roland Garros.

In an exclusive interview with Tennishead, Kevin Anderson discussed which of the ‘big three’ players he found the toughest to compete against.

Kevin Anderson says he found Roger Federer tougher to play against than Novak Djokovic and Rafael Nadal

“It’s kind of pick your poison on that one. Each one had their own set of challenges,” Anderson, a two-time major finalist, told Tennishead.

“At some point in time all three of them were these big entities of… so much press and big occasions surrounded all of them.

“So from that standpoint, I found them all challenging.”

“From an actual game standpoint, in terms of matchup, I would say the one that I thought was probably most challenging was playing [Roger] Federer.

The Championships - Wimbledon 2009 Day Thirteen
Photo by Paul Gilham/Getty Images

“Just with his style and the amount of variety he had.”

Federer, who retired from his playing career in 2022, won 20 Grand Slam titles during his illustrious career – including a record eight Wimbledon Men’s Singles titles.

Kevin Anderson’s best Grand Slam performances

Anderson, who recently joined the Advisory Board at INTENNSE, was one of only 12 men to defeat Federer at the All England Club.

Anderson won a marathon 2018 Wimbledon quarter-final against the Swiss maestro, 2-6, 6-7, 7-5, 6-4, 13-11.

Kevin Anderson of South Africa and Roger Federer of Switzerland embrace at the net following their Men's Singles Quarter-Finals match on day nine of the Wimbledon Lawn Tennis Championships at All England Lawn Tennis and Croquet Club on July 11, 2018 in London, England. Anderson won the match 6-2, 7-6, 5-7, 4-6, 11-13 in 4hr 13min.
Photo by Michael Steele/Getty Images

The South African went on to reach the final, before losing to Novak Djokovic.

Anderson clarified his stance on Federer’s game, explaining that he found the Swiss maestro difficult to play on any surface, rather than just grass.

The former world number five also delved into his difficulties in managing the occasion, admitting that he had often lost matches against the big three before stepping onto the court.

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Carlos Alcaraz and Jannik Sinner at the ATP Finals in 2025

““I would say just in general,” Anderson said of Federer’s all-court game.

“To be quite honest, my biggest challenge was more just dealing with the occasion as opposed to the actual opponent.

“Obviously, all of them are really tough players to face, but each one of them respectively, of all the matches I played.

“Unfortunately I was really was not able to bring anywhere near the kind of tennis that I was capable of playing to give myself a fair matchup.

“Most of those matches, looking back at it, kind of the match was – not all of them – but a lot of them were kind of lost before I got onto the court.

South Africa's Kevin Anderson returns against Switzerland's Roger Federer during their men's singles quarter-finals match on the ninth day of the 2018 Wimbledon Championships at The All England Lawn Tennis Club in Wimbledon, southwest London, on July 11, 2018.
Photo credit should read OLI SCARFF/AFP via Getty Images

“But that’s the tough part. You’ve got a few players who you’re playing in these big environments.

“But I’d say just for the most part, playing Novak, lost to him a whole bunch of times, but I feel like I played some really good matches against him.

“Whereas Federer rarely… of all the times I played him, it was only when I beat him at Wimbledon – obviously that was a really close match – but the rest of the time, I was really unable to play the kind of tennis I wanted to play.”

Anderson, the former world number five, also recently reacted to Jannik Sinner’s stunning defeat at Roland Garros.

Kevin Anderson discusses his admiration for Joao Fonseca

Anderson also discussed the development of a player who has often been compared to Roger Federer: Joao Fonseca.

Fonseca, 19, has quickly emerged as one of the brightest young talents on the ATP Tour over the past year.

The Brazilian youngster, whose idol is Roger Federer, has enjoyed his best run at a Grand Slam over the past fortnight, beating Novak Djokovic and Casper Ruud on his way to the Roland Garros quarter-finals.

João Fonseca of Brazil salutes Novak Djokovic of Serbia after their match during the Men's Singles on Day Six of the 2026 French Open at Roland Garros on May 29, 2026 in Paris, France.
Photo by Antonio Borga/Eurasia Sport Images/Getty Images

Anderson, who spoke to Tennishead ahead of Fonseca’s third-round victory over Djokovic, discussed the development of Fonseca’s game and offered his thoughts on two other young ATP starlets.

“I was really impressed with Fonseca from the beginning,” Anderson said. “I feel like, just the temperament, the big match mentality – he’s often playing in front of people.

“I feel like he’s still got some work to do developing his game and it will be interesting to see if he can balance the success that he’s already had with identifying the areas of improvement for him to start going deeper in Slams.

How many Grand Slam titles will Joao Fonseca win in his career?

What a match!

“He’s obviously very young, around 19 or 20, but [in] prior years you’ve had also young people like that who have had more success than he has. So he’s still figuring it out.

“Moise [Kouame] is just, I mean, breaking through right now. I saw him playing a junior tournament a couple of years ago.

“He’s very physical. But still, I think he’s got a lot of work to do in his game to have consistency. It goes without saying, because he’s so young.

Moise Kouame reacts during his match against Alejandro Tabilo at Roland Garros in 2026.
Photo by Ibrahim Ezzat/NurPhoto via Getty Images

“And [Rafael] Jodar – I’ve only really seen him just with highlights a little bit, so it will be interesting to see his progression.

“But he’s been on a terrific run these last few weeks, and breaking through… it seems like he’s definitely one to watch.”

Anderson, who recently discussed the ongoing prize money debate in tennis, has embarked on a new project.

The South African has joined INTENNSE – a league that adopts a different format to your run-of-the-mill tennis match.

Players are only allowed one ball toss and one serve per point, and the team that wins the most points over the three non-stop 10-minute periods wins the overall contest.

Teams consist of eight individuals – four men and four women – with unlimited substitutions allowed.

Kevin Anderson selects his career highlight

Kevin Anderson enjoyed a stellar career on the ATP Tour, winning seven titles and qualifying for two Grand Slam finals.

The South African also achieved the world number five ranking, becoming one of the greatest players in South African tennis history.

However, Anderson selected another moment as his career highlight.

“If I had to pick one, it would be my run to the Wimbledon final,” the 40-year-old told Tennishead.

Kevin Anderson of South Africa celebrates his victory over John Isner of The United States after their Men's Singles semi-final match on day eleven of the Wimbledon Lawn Tennis Championships at All England Lawn Tennis and Croquet Club on July 13, 2018 in London, England.
Photo by Matthew Stockman/Getty Images

“It’s just such a… especially after tennis when you move on, you just get to see this kind of magnitude and difference between the majors and the rest of the Tour.

“From a career highlight, it’s something that, outside of all the tennis… the percentage of people who know that versus anybody else is very little.

“But if I sit back at it, it was a great few weeks being at Wimbledon. Had a lot of family and friends coming over. There’s a lot of memories to recount from that.

“I had really good matches throughout the whole two weeks. Played a lot of good opponents, played a lot of tennis. So that would definitely be up there.”

Anderson, seeded eighth at the 2018 Wimbledon Championships, defeated Gael Monfils, Roger Federer and John Isner on his way to the final.

As already mentioned, Anderson’s victory over Roger Federer was particularly emphatic, as he defeated the Swiss maestro 13-11 in the fifth set.

In the final, Anderson was defeated by Novak Djokovic in straight sets, 2-6, 2-6, 6-7.