The Top 5: Cross-Generational Matchups

TC LIVE: Serena's US Open expectations

In 1999, Serena Williams claimed the singles title at the US Open, the first of her 23 Grand Slam victories.

Emma Raducanu, the defending champion in New York and Williams’ first-round opponent in Cincinnati, was still a few years away from taking the court then, to say the least, considering she was born in 2002.

In their blockbuster encounter, youth was definitely served as Raducanu topped Williams 6-4, 6-0, dashing the American’s chances at building momentum before what is expected to be her last tournament, the US Open.

It’s always hard to predict the score between a young prodigy and a seasoned veteran: It’s usually a toss-up, and Williams has found herself playing both roles at different points over the course of her illustrious career. Here’s a look at several other cross-generational clashes through the years.

Tracy Austin vs. Chris Evert, 1977

Evert’s baseline game built around never-seen-before consistency inspired a whole generation of young girls, among them a teenager from California who would go on to become one of her biggest rivals for a time. When Evert met Austin, 14, in the third round of Wimbledon in 1977, the match was quickly decided in the 22-year-old’s favor. Austin notched her first win against Evert in their fourth match, and would go on to lead their head-to-head contests.

Andre Agassi vs. Jimmy Connors, 1988

By the mid-1980s, the search was on in a major way for the next great American hope who would pick up the torch passed down from John McEnroe and Connors. The brightest star on the horizon in the second half of the decade was Agassi, who, in 1988, firmly established himself as a member of the top 10 at only 18 years old. When Agassi and Connors played for the first time at the US Open, the younger American topped the five-time champion in the semifinals in straight sets.

Serena Williams vs. Stefanie Graf, 1999

Greatness was expected of Serena and Venus Williams from an early age, and by the later years of the 1990s, they were well on their way. First, though, they had to contend with the veterans who were still dominating the game, like Graf. The German—a former teen prodigy herself—and Serena Williams faced each other for the first time at the 1999 tournament in Sydney, Australia, in a three-set battle won by Graf. A few months later, the tables were turned as Williams defeated Graf in the Indian Wells final in three tough sets for the biggest win of her burgeoning career.

Roger Federer vs. Pete Sampras, 2001

In 1998, Federer won the title at the boys’ edition of Wimbledon, the same season Sampras picked up his fifth victory in six years at the senior level. Three years later, the two all-court stylists would clash in the fourth round of the men’s event in what would be one of the biggest passing-the-torch moments in the history of the sport. Going back and forth over the first four sets, it was widely assumed the veteran Sampras would come out on top in the fifth. Seemingly unfazed by the situation, however, the 19-year-old Swiss clinched the decider 7-5 for a statement win.

Rafael Nadal vs. Carlos Moya, 2003

After an Australian Open final, a French Open victory and a stint atop the men’s rankings, Moya put the tiny Spanish island of Mallorca on the map, with his results leaving a lasting impression back home. One of the players he inspired happened to be none other than Nadal, and in 2003, the pair faced off for the first time at the Masters 1000 tournament in Hamburg, Germany. Only 16 at the time, Nadal beat his hero in straight sets to announce himself as a future star. And the relationship continues with Moya to this day as the former veteran is now coaching the future Hall of Famer.