On this day, 1999: Roger Federer makes his Grand Slam debut in Paris

On May 25, 1999, a 17-year-old Swiss stepped onto Court Suzanne Lenglen for the first Grand Slam match of his career, falling quietly to then-No. 3 Patrick Rafter in the first round of the French Open.

That Swiss teenager, Roger Federer, would go on to become one of the greatest players of all time.

Those who’d been paying attention at the time knew Federer was incredibly talented. He’d been a top junior, winning the Wimbledon boys’ title in 1998 and reaching No. 1. And he had already made a strong first impression on the main tour, reaching three ATP quarterfinals and scoring his first Top 10 win earlier in the year with an upset over No. 5 Carlos Moya at an indoor event in Marseille.

But he hadn’t won a tour-level match on clay yet, and Rafter was just too experienced.

The Australian may be best remembered for his results on faster courts, winning back-to-back US Opens in 1997 and 1998, and making two Wimbledon finals in 2000 and 2001. He was no slouch on clay either, reaching the Rome final a few weeks earlier, as well as the French Open semis in 1997.

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Federer, a 111th-ranked wild card, managed to sneak out a tight first set, but Rafter had no trouble from there, cruising to a 5-7, 6-3, 6-0, 6-2 victory after two hours and 13 minutes. The third and fourth sets lasted a total of just 52 minutes.

At Roland Garros last year, Federer was asked about that match against Rafter.

“I was really happy to play against Rafter, who was one of the most popular players on the tour,” he said. “He had this aura of being nice and fair play, so it was great being able to play him on Suzanne Lenglen Court rather than on Court 23. So I played a good match. I wanted to play on a big court.

“It didn’t happen, but nevertheless it was a great experience for me.”

Federer would end up losing his first 11 tour matches on clay before finally winning his first three matches in a row on the surface at Roland Garros a year later, reaching the fourth round before falling to Alex Corretja.

Fast forward 21 years, and that clay-court learning curve is a distant memory. Federer isn’t just a French Open champion now, lifting the Coupe des Mousquetaires in 2009, but he’s been to another four finals on the terre battue, as well as three more semifinals and four more quarterfinals.

He’s also won six of his 27 career ATP Masters 1000 titles on clay—four in Hamburg and two in Madrid.

But in the big picture, Federer is now a 20-time Grand Slam champion, averaging out to just under one a year since his debut against Rafter 21 years ago.