For the first time this millennium, Roger Federer won’t play in the U.S. Open. 

The last U.S. Open main draw without Federer came in 1999, when he lost in the second round of qualifying to fellow Swiss player Ivo Heuberger.

For some perspective: During the 1999 U.S. Open, Frances Tiafoe was one year old. The No. 1 song in the United States was “Bailamos” by Enrique Iglesias. Barack Obama was in his second term as an Illinois state senator. Donald Trump was merely considering running for President, not actually running. 

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The world today is clearly a different place. But while the vast majority of male competitors at the ’99 Open have long since retired, a few are still going on the ATP Tour. (Side note: Serena Williams also competed (and won) the U.S. Open in 1999, and she's scheduled to play in this year's tournament, but we're sticking to male players for this exercise.)

Here’s a look at the five current active male players who also participated in the 1999 U.S. Open singles main draw. 

Bob Bryan

The doubles legend only appeared in a handful of Slams as a singles player. After making the second round of the 1998 U.S. Open, he returned in 1999 as a wildcard and fell in the first round to Magnus Larsson in four sets. Bryan would go on to play as a wildcard in the singles draw the following two years, losing in the open rounds. His doubles career hasn’t been half-bad, though—he has a paltry 16 Grand Slam titles to his name.

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Tommy Haas

Seeded No. 14 at the 1999 Open, Tommy Haas reached the fourth round before bowing out to Frenchman Cedric Pioline in the fourth round. Since turning pro in 1996, Haas has won 15 singles titles and more than $13 million in prize money. The German most recently played an event last October in Vienna, and is currently recovering from toe surgery. In June, he was named the new tournament director for Indian Wells. He and Roger Federer are good friends, but their friendship has been one-sided on the court: Federer leads their overall head-to-head 13-3, including a Federer victory in the 2009 Wimbledon semifinals.

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Daniel Nestor

Nestor arrived in New York for the 1999 U.S. Open on the heels of his best finish ever in a major singles draw: a fourth–round appearance at Wimbledon. But Nestor couldn’t replicate his success at the year’s final Slam, falling in the first round to Italian veteran Gianluca Pozzi. Nestor, now 43, has been an incredibly successful doubles player, reaching No. 1 in 2002 and winning 90 career titles, including eight Slams. He also won gold for Canada at the 2000 Olympic Games.

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Takao Suzuki

Suzuki turned professional in 1995, and he appeared in the U.S. Open main singles draw as a qualifier in 1999. John van Lottum ousted him in the first round, but Suzuki gave him a tough match, winning one set and losing two others in competitive tiebreakers. Though Suzuki has never cracked the top 100, he’s still grinding away on tour. Suzuki, 39, last appeared in the Guam F1 in May, beating Japanese compatriot Yuichi Ito in the first round before losing to Deiton Baughman. Fun fact: Suzuki met Federer as a qualifier in the second round of the 2005 Australian Open. (That’s where the fun ends—Federer beat him 6-3, 6-4, 6-4. Though Suzuki did take a set off Federer in Tokyo in 2006.) Suzuki is currently ranked No. 1,140.

Max Mirnyi

The 1999 U.S. Open was just Mirnyi’s second Grand Slam event, and he exited in the second round to No. 3 seed Yevgeny Kafelnikov. Three years later, Mirnyi made the quarterfinals in Flushing, his best finish ever in a major singles draw. The Belarusian is an accomplished doubles player: He’s won six Grand Slam doubles events and achieved a No. 1 ranking in 2003.

 

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