Chris Evert vs Martina Navratilova

Easily the oldest rivalry on this list (1973-1988), Chris Evert and Martina Navratilova slugged it out on the tennis courts for about a decade and a half, with Navratilova having the edge over her rival, 43 wins to 37. The fact that Martina Navratilova then went on to have another lengthy rivalry with Steffi Graf from 1985 to 1994 only goes to show how transcendent she truly was as a tennis icon.

Novak Djokovic vs Rafa Nadal

Pretty much every permutation of the Novak-Rafa-Roger triumvirate has to go on this list, just because we tennis fans have been *that* spoiled for superstars in our sport. Tiger Woods wishes he had two equally worthy rivals during his run. Like a game of Rock, Paper, and Scissors, Novak is the scissors to Rafa’s paper, having the narrow edge of 27 wins to Rafa’s 25. Seeing as this has been going on since 2006, it’s amazing how it seems like the rivalry can just go on forever. These two were also the first two men to face each other in all four Grand Slam Finals.

Serena Williams vs Venus Williams

Twenty-one years. The fact that this rivalry has lasted 21 years on the courts doesn’t tell the whole story: Serena and Venus have been sisters and rivals since birth, without a doubt. Two of the most talented tennis players of all time who just happened to be sisters, these two have really taken it to each other, although Serena holds the advantage head-to-head, 17 to 12. Nonetheless, Serena holds 23 Grand Slam titles, which is an all-time mark, while Venus holds 7, which is nothing to sneeze about. If this matchup weren’t a bit lopsided, this would easily have been the best tennis rivalry of all time.

John McEnroe vs Bjorn Borg

Sporting an even 7-7 record, this short-lived but storied rivalry was an exercise in contrasts. With McEnroe’s fiery demeanor and Borg’s icy calm, the two were an even match across their run. It shouldn’t come as a surprise that this storied rivalry both became a film in 2017, as well as the unofficial inspiration for parts of the hilarious Heder-Ferell comedy, Blades of Glory. Think of the Fire and Ice routine, plus Jimmy McElroy’s name sounding a whole lot like John McEnroe.

Novak Djokovic vs Roger Federer

Novak Djokovic must be a really strong pair of scissors, because his scissors beat both Nadal’s paper and Federer’s rock narrowly, in this case, 24 to 22. Despite his apparent advantage over both men head to head, both men still have more grand slam titles than he does, but he’s not too far behind. With Djokovic’s Wimbledon win, make that 25 to 22.

Steffi Graf vs. Monica Seles

This decade-long rivalry may have Steffi Graf in the lead on their head to head matchups, but it was the sheer spectacle of the near-tragic stabbing incident by a crazed Steffi Graf fan that permanently hindered Monica Seles that highlights just how intense this rivalry was. While we can imagine how different this rivalry might have been had the stabbing never happened, it’s also the stabbing that brings more prominence to this rivalry than what it would have otherwise gotten.

Pete Sampras vs. Andre Agassi

With 13 years of history, the Sampras-Agassi rivalry is nothing short of storied and remarkable. Sampras holds a 20-14 advantage over Agassi, but Agassi’s flamboyance on and off the court made tennis cooler in the ‘90s, which is not something you can often say about the sport at the time.

Roger Federer vs Rafa Nadal

When you have two men who are in heavy consideration for their sport’s G.O.A.T. status matching up with one another as often as these two do, you just know you’re always in for a treat. Roger Federer and Rafa Nadal have been at it since 2004, with no signs of slowing down, even if Nadal does hold the edge over Roger head to head, 23 to 15. Despite their head to head record, after all, Roger has 20 Grand Slam titles, while Rafa holds only 17.

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