When Rafael Nadal put away the final overhead in his first-ever match against world No. 1 Roger Federer at the 2004 Miami Open, the commentator, John Barrett, delivered one of the most prescient and spine-tingling sign-offs you will ever hear.

“A quite astonishing win by a young man who’s progress is so fast, so rapid, that one wonders where it will all end.”

Fast forward more than 16 years and you will find both Federer and Nadal tied atop the all-time men’s Grand Slam title list with 20 apiece. Barrett was clearly on to something, because we’re still wondering.

Along with Novak Djokovic, it’s tough to argue against the current Big 3 era being tennis’ greatest generation, with Rafa, Roger and Nole dominating nearly every measurable statistic. And while it’s fun to compare different eras and generations, it remains an exercise in futility.

Tennis author and historian Joel Drucker raises an excellent point. “How can you rate players by how many majors they’ve won—and that’s how Federer, Nadal, and Djokovic will be rated—when the best male player of the 1950s, Pancho Gonzalez, was banned from playing them for nearly his entire career?”

Across Generations: Appreciate the tennis, but leave comparisons aside

Across Generations: Appreciate the tennis, but leave comparisons aside


Rafael Nadal at the 2004 Miami Open, playing Roger Federer for the first time. (Getty Images)

Today's player reap the benefit of groundbreaking, career-extending sports science and recovery breakthroughs that previous generations lacked. Not to mention the numerous technological advancements that have evolved the game throughout the past 50 years, perhaps more so than any other sport. But every now and then, when the stars align, we are lucky enough to witness matches between the different generation’s greatest players.

Pete Sampras and Federer faced off just one time, but it remains one of the most significant matches in tennis history. A true clash of styles, and a de facto changing of the guard (though Federer wouldn't win his first Grand Slam title for another two years), it won by the Swiss, 7-5 in the fifth set in the fourth round of the 2001 Wimbledon Championships.

Another memorable cross-generational meeting occurred in 2003 in Hamburg, when a 16-year-old Rafael Nadal defeated world No. 4 Carlos Moya (his idol and future coach) in straight sets. Moya was well aware of his countryman’s bright future, but he wasn’t prepared for Nadal’s geometrically game-changing combination of spin, power and speed.

Prior to this match, Moya and Nadal had shared a practice court many times.

“I understood that it was one of the many times that he would win and I knew he was going to be a great player,” Moya said.

But it would be impossible to predict just how meteoric Nadal’s rise would be.

Across Generations: Appreciate the tennis, but leave comparisons aside


While these encounters are a beautiful aspect of tennis history, it’s important to remember that the head-to-head record almost always favors the younger player. From Rod Laver to Jimmy Connors, Bjorn Borg to John McEnroe, Boris Becker to Andre Agassi, and Chris Evert to Martina Navratilova, the younger great owns the head-to-head advantage. Federer trails Djokovic 23-27 in their career, but at one point he owned a 7-2 advantage.

Djokovic won his first five matches against Dominic Thiem, but has since lost five of his last seven. If Thiem finishes his career with a positive record against Djokovic (and I believe he will) that doesn’t mean Thiem was better than Djokovic, it means he experienced his physical and mental peak while Djokovic experienced his inevitable decline. There are, of course, exceptions to this rule. Ivan Lendl owns a 6-2 record over Andre Agassi, a player 10 years his younger. Only Father Time is undefeated.

As we enjoy these cross-generational matchups, it’s important to remember that they don’t occur very often, and when they do, there’s no way to know their significance until many years later. So when you are blessed with a match like Jannik Sinner vs. Rafael Nadal in the Roland Garros quarterfinal, or Sampras vs. Federer at Wimbledon, it’s best to leave the comparisons aside and simply enjoy the tennis, as difficult as that may be.

Monday 11/30:

2009 Shanghai second round: Rafael Nadal vs. James Blake

2016 Stuttgart second round: Roger Federer vs. Taylor Fritz

2019 Roland Garros third round: Sofia Kenin vs. Serena Williams

2019 Wimbledon first round: Coco Gauff vs. Venus Williams

Tuesday 12/1:

2004 Cincinnati semifinal: Andre Agassi vs. Andy Roddick

2017 Montreal fourth round: Denis Shapovalov vs. Rafael Nadal

2019 Shanghai quarterfinal: Alexander Zverev vs. Roger Federer

Wednesday 12/2:

2019 US Open final: Bianca Andreescu vs. Serena Williams

2019 Australian Open quarterfinal: Stefanos Tsitsipas vs. Roger Federer

2019 Madrid second round: Alexander Zverev vs. David Ferrer

Thursday 12/3:

2001 Wimbledon fourth round: Roger Federer vs. Pete Sampras

2003 Hamburg second round: Rafael Nadal vs. Carlos Moya

2003 Houston round robin: Andre Agassi vs. Roger Federer

Friday 12/4:

2005 US Open final: Roger Federer vs. Andre Agassi

2018 Toronto final: Stefanos Tsitsipas vs. Rafael Nadal

2019 Roland Garros quarterfinal: Amanda Anisimova vs. Simona Halep

2020 Australian Open first round: Coco Gauff vs. Venus Williams