Roger Federer, Rafael Nadal, and Novak Djokovic dominated tennis for over two decades in the 2000s and 2010s.
Rafael Nadal, Roger Federer, and Novak Djokovic won 66 Grand Slam titles between them, leaving little space for other tennis stars to land major titles.
Others were trying to crack the impenetrable glass ceiling created by the three tennis superstars, with Andy Murray coming closer to getting near them.
Stan Wawrinka was another star who managed to snag Grand Slams from the trio, and he’s named the toughest opponent out of the three.

Stan Wawrinka revealed Rafael Nadal was toughest opponent
Wawrinka was one of the best tennis players of any generation, but unfortunately for the Swiss star he came up against Federer, Nadal, and Djokovic.
The star was never able to crack the top 2 of the rankings, but he did pick up three Grand Slam trophies at the Australian Open, Roland Garros, and the US Open between 2014 and 2016.
Asked who was the toughest to play against out of Nadal, Federer, and Djokovic, the Swiss star instantly opted for one name.
“Well, they have all been so tough, but I think Rafa at the French Open was particularly challenging,” he said on the Nothing Major podcast.
Wawrinka met Nadal in the final of Roland Garros in 2017, losing to the King of Clay in a straightforward straight sets contest.
“I was constantly watching the clock,” explained Wawrinka. “Hoping to reach the one-hour mark before he won.”
Wawrinka, who was the oldest finalist since Ken Rosewall in 1968, lasted two hours and five minutes against Nadal.
“It’s especially tough with his high backhand shots coming at you nonstop,” added the former World No. 3.
“You feel like every single ball is coming at you, and you don’t see any option to hit a winner or push him out of the court.”
Nadal won 22 Grand Slams, with 14 of those coming at Roland Garros between 2005 and 2022.
When will Novak Djokovic join Roger Federer and Rafael Nadal in retirement?
The only player of the three still playing competitive tennis is Djokovic, who is incredibly still the World No. 6.
Nadal called time on his tennis career in 2024 after the Paris Olympics, while Federer retired in 2022 following the Laver Cup.
There have been a few signs that Djokovic could be about to join his long-time rivals, especially after his Roland Garros defeat to Jannik Sinner.
After losing to the World No. 1 in straight sets, the Serbian said: “This could have been the last match I played here, so I don’t know. That’s why I was a bit more emotional even in the end.”
“Do I wish to play more? Yes, I do,” said Djokovic defiantly, but he admitted it may not happen. “Will I be able to play in 12 months’ time here again? I don’t know.”
Djokovic has not won a Grand Slam since capturing the US Open in 2023.
