Roger Federer prepares for a backhand at the 1999 French Open.

Ambitious as Roger Federer has always been, even he had no idea there were 420 more Grand Slam matches in his future—including a record 20 major singles titles. All the 17-year-old Federer knew on this day in 1999 was that he was at Roland Garros and primed to play in the main draw of a major singles tournament for the first time.

The previous year, Federer had been the world’s best junior, most visibly so when he’d triumphed at Wimbledon. At the end of 1998, the rookie pro from Switzerland was ranked 302 in the world.

The first five months of ’99 saw him make considerable progress, Federer propelled up the ranks courtesy of fine results at Challenger and ATP events. That February, Federer reached two straight quarterfinals at ATP tournaments. The first came in Marseille, highlighted by a win over the reigning Roland Garros champion, Carlos Moya. Later that month, in the last eight of Rotterdam, Federer stretched recent Australian Open winner Yevgeny Kafelnikov, losing the match 6-1, 5-7, 6-4.

By late May, Federer’s ranking had soared to No. 111. He was awarded a wild card entry into Roland Garros. Still, at that point Federer had yet to win an ATP tour match on clay.

Years later, Federer’s toughest opponent in Paris was, of course, the greatest clay court player ever, Rafael Nadal. But for this clay court debut, the matchup was quite different: the formidable net-rusher, third-seeded Patrick Rafter. Federer met Rafter during the Aussie’s richest part of his career—two straight US Open titles in ’97 and ’98. Rafter was also quite skilled on clay, having recently reached the finals in Rome and the semis at Roland Garros two years prior.

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Roger Federer serves at the 1999 French Open.

Roger Federer serves at the 1999 French Open.

Federer and Rafter entered Court Suzanne Lenglen. Back then, Federer wore his hat backwards and was prone to far more displays of emotion, given to shouting out to himself and, in this match, even throwing his racquet.

Enjoying the advantage of an opponent’s lack of familiarity with his game, the eager teen surprised Rafter and won the first set, 7-5.

“It took a little bit of time to adapt to him,” Rafter said in a 2018 Tennis World story written by Luigi Gatto. But quite quickly, much changed. As Rene Stauffer explained in his book, The Roger Federer Story, Quest for Perfection, “the sun came out and the conditions became warmer and faster. The clay courts dried out and balls moved much faster through the court. The Australian’s attacking serve-and-volley style seemed to run on automatic and he won in four sets.” The final score: 5-7, 6-3, 6-0, 6-2.

“The boy impressed me very much,” said Rafter. “If he works hard and has a good attitude, he could become an excellent player.”

Years later, talking with New York Times tennis writer Christopher Clarey, Federer recalled the match. “After the first set, said Federer, “he got the hang of how I play and he, like, sliced and diced me.”

The French sports newspaper L’Equipe also noted Federer’s considerable potential, noting that, “The young man from Switzerland could be one of the people who will shape the next ten years.”

To the world’s joy, that guess was off by a decade.