The 5 Greatest Rivalries in Men’s Singles Tennis History

When it comes to professional tennis, there are usually two or three people that are dominating the field at any given time. Because of this, you tend to see the same faces reach the finals of every major tournament, but it’s not usually one-sided. Instead, it has made for some great back-and-forth rivalries with all-time greats duking it out to see who is really the best.

Which rivalries in men’s tennis are truly the greatest, though? Today, we’ll examine the five best, but not in order of the most matches played or most grand slam finals at stake. Instead, we want to focus on the intensity of the rivalries between legends, even if there were barely a dozen matches played between the two. 

Novak Djokovic vs. Rafael Nadal

Three men dominated tennis for the first couple of decades in the 21st century, so it was hard to pick how the round-robin rivalries stacked up against one another. Of course, we’re talking about Novak Djokovic, Rafael Nadal, and Roger Federer, and for the start of the list, Federer is left off. That’s because Rafa and Joker have played each other more than any other duo in the open era and it’s an almost 50-50 split in the record.

The rivalry has been intense, though there’s a certain ‘it’ factor that leaves it lower on the list. After all, the two have also had more grand slam matches and grand slam finals matches than any other pairing. Both men have gone on hot streaks against the other throughout this rivalry, including two seven-match win streaks by Djokovic to even things up in their history.

Ken Rosewall vs. Rod Laver

There’s one rivalry from before the Open Era on the list, and it’s between Australian legends Ken Rosewall and Rod Laver. Early on in their careers, the two men would play each other seemingly every week, and they had 164 total professional matches against each other, with more than 200 estimated when you include exhibition matches. In 1963 alone, they had 51 professional matches with Rosewall winning 38 of them.

Laver would get better almost immediately after that year, though, and ended up taking the overall series 89-75 over his long-time rivals. “Ken has consistently been my toughest opponent, on any surface,” Laver said, adding that “Ken pushed me around for about 20 years.” If you take out their first year playing each other, Laver actually held a 76-37 series advantage.

Jimmy Connors vs. John McEnroe

Tennis may be considered more of a European sport, but two of the best rivalries in men’s history have been between two Americans. The first of those rivalries on the list is between Jimmy Connors and John McEnroe, with the two men holding a combined 15 grand slam championships. 

Both of these men had rivalries with Bjorn Borg that were considered to be all-time greats, but against each other, there was a certain extra level of intensity. Connors and McEnroe squared off 34 different times professionally, including nine times in a grand slam. Two of those were in the finals, with each getting one win. “To have carried on this rivalry for so many years…must mean that we made our mark somewhere,” Connors said.

Pete Sampras vs. Andre Agassi

The other American rivalry to make the list was between perhaps the two greatest players that the country has ever produced. However, Sampras is considered the best in United States history, and he was a constant thorn in Agassi’s side as he tried to reach the mountaintop. Sampras and Agassi played their first match in 1989 and would meet up 34 times in total.

Sampras won 20 of those matches, including four of the five times when they met in a grand slam final. The first one came with Sampras sweeping the 1990 US Open, but Agassi would notch things up in 1995 at the Australian Open. Sampras dominated in their final three meetings, though, including a pair of US Opens.

Roger Federer vs. Rafael Nadal

There is a lot of debate about who the best men’s tennis player of all time is, and that conversation is usually between Roger Federer and Rafael Nadal. The two just happened to play in the same era of tennis, meaning that they were able to prove who was best repeatedly. The two men played in 40 professional matches, including nine in grand slam finals.

Some might be surprised to learn that Nadal actually holds the advantage with 24 wins, including six in grand slam finals. The two needed each other to validate their careers, and they acknowledge that it meant a little more when they played each other. “It was different from other matches,” Nadal said.