From history-making upsets to future Hall of Famers making their Grand Slam debuts, many a noteworthy accomplishment has been made during the first round of the French Open. Here’s a look at five of them from the sport’s most prestigious clay-court tournament.

1

An Upset of Epic Proportions

Even though it had been nine years since her first French Open victory, Serena Williams entered the 2012 tournament as the heavy favorite, having won two tournaments on the dirt during the spring stretch. Taking on Frenchwoman Virginie Razzano in the first round, Williams easily won the first set over the world No. 111, then had multiple chances to put the match away in the second. Razzano rallied to take the tiebreaker to push the match into a decider, and with the support of the home crowd behind her, she won the third set 6-3, dealing Williams her first—and, to date, only—opening-round loss at a major.

2

A Star Is Born

The most memorable 
Roland Garros first 
rounds in history

The most memorable Roland Garros first rounds in history

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With an ankle problem keeping him out of the 2004 French Open, young Spaniard Rafael Nadal had to wait until 2005 to make his tournament debut. Riding a wave of momentum rarely seen in the history of the sport, Nadal was established as a favorite for the title, but he still had to get past the first round. In his opener, Nadal faced a veteran, Lars Burgsmuller of Germany, and won in straight sets. From there, he’d go on to win the 2005 edition—and 11 more times after that.

3

One and Done for the Top Two

The most memorable 
Roland Garros first 
rounds in history

The most memorable Roland Garros first rounds in history

After three-time champion and world No. 1 Ivan Lendl decided to skip the 1990 edition of the tournament, No. 2 Stefan Edberg and third-ranked Boris Becker ascended to the first and second spots in the draw. Renowned for their success on grass, the serve-and-volleyers had just battled it out in the 1989 Roland Garros semifinals, with Edberg beating Becker in five sets. However, a year later, the top two were knocked out of the tournament by teenagers Sergi Bruguera and Goran Ivanisevic, respectively— both of whom would go on to win Grand Slam titles in their careers.

4

Wild Times for Monfils

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The most memorable 
Roland Garros first 
rounds in history

The most memorable Roland Garros first rounds in history

One of France’s most dynamic players, Gael Monfils needed a wild card to get into the 2013 French Open due to injury knocking him out of the top 100 at one point. Coming in to the tournament, though, on the heels of a title at the Bordeaux Challenger and a final-round showing in Lyon, Monfils was in good form. Facing the fifth seed Tomas Berdych in the opening round, the Frenchman rallied from two sets to one down to take the match in five, much to the delight of the home crowd.

5

The March to History Begins

The most memorable 
Roland Garros first 
rounds in history

The most memorable Roland Garros first rounds in history

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Only a few months after finishing 1998 as the No. 1 junior in the world, 18-year-old Roger Federer made his main-draw Grand Slam debut at the French Open. Ranked No. 111 going into the 1999 edition of the tournament, the young Swiss faced two-time US Open champion Patrick Rafter in the first round. After claiming the first set, Federer ended up losing in four, but would go on to rewrite the record books, eventually completing the career Grand Slam 10 years later in Paris.