Sports News Without Fear, Favor or Compromise
Sports News Without Fear, Favor or Compromise

With millennials headed for the nursing home, let’s revisit the Osaka-Williams rivalry and other great generational clashes

Millennials BTFO
Millennials BTFO
Photo: Getty Images

Naomi Osaka has faced Serena Williams five times now, and the 23-year-old’s straight-sets victory in Thursday’s semifinal at the Australian Open marked the third win for the three-time (so far) major champion over the 23-time (so far) major champion, including both of their meetings at Grand Slam events.


Williams had the upper hand in their last two encounters, in the 2019 Rogers Cup quarterfinals and this year’s A Day At The Drive championship. But not this time.

While Williams and Osaka have been squaring off since 2018, when they first played each other at the Miami Open — a first-round upset by Osaka as she began to assert herself en route to winning that year’s U.S. Open over Williams — each time they play each other now takes on added significance. Osaka clearly looms as a dominant force on the WTA Tour for years to come, while Williams — still a top player in her own right as the current No. 11 player in the world — is, it’s fair to say, on the back end of her career.

Time was, Williams was on the other end of this kind of pairing, as she had two matches with Steffi Graf in early 1999, the last season of the 22-time Slam winner’s career.

Graf won their first meeting, in the second round of the Adidas International in Sydney…

...while Williams got the upper hand when they met two months later in the final at Indian Wells.

The same year, Williams knocked off Monica Seles in the U.S. Open quarterfinals, one of five meetings between them, with four won by Williams.

That victory over Seles was followed by the 17-year-old Williams beating Lindsay Davenport and Martina Hingis to win the first of her six (so far) U.S. Open titles, and the one that enabled her to be in position to become a Grand Slam champion in four different decades whenever she adds another trophy to her collection.

Running it back further, Graf had a lot of overlap with Martina Navratilova and Chris Evert, as they were at the peak of their powers when Graf turned pro in 1982. Likewise, Navratilova playing as long as she did meant that she had 16 meetings with Seles, who won nine of them. But Seles and Evert? They only opposed each other three times, each winning once before their rubber match in the 1989 U.S. Open round of 16.

Youth is not always served, alas. But sometimes, discretion is the better part of valor for an old head. In 2013, Mariano Rivera faced Mike Trout for the first and only time. Protecting a 6-5 lead, the greatest closer in history issued a walk to Trout, loading the bases to bring up Albert Pujols, who struck out to end the game.

Generational clashes aren’t limited to sports where you can go one-on-one. In 2001, Tom Brady threw an interception to Antoine Winfield of the Bills, a play that did not make the ESPN NFL Primetime highlights, although a pass interference penalty against Winfield did.

Winfield’s son, Antoine Jr., just won the Super Bowl as Brady’s teammate.

Elsewhere on the GOAT scene, Michael Jordan retired right before LeBron James came into the NBA, but James’ rookie year was the same season as the last campaign of Scottie Pippen and Karl Malone… neither of whom played against the Cavaliers that year.

In that case, how about Jordan as a rookie against not only Magic Johnson and Kareem Abdul-Jabbar, but a Lakers team that also featured Bob McAdoo?

Time marches on. It’s fun when we get to these intersections.

Sorry to all the other Jesse Spectors for ruining your Google results.