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WATCH: Andy Roddick Admires Holger Rune For Masking Thirst Trap As Workout Video.

As the 2023 US Open progresses, we will continue to note and hear that it’s been 20 years since an American man won a Grand Slam singles title. That happened when Andy Roddick won the 2003 US Open. Since then, there have been several notable runs to the semis and finals of majors.

Without further ado, our "Top" 10, in chronological order:

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"It's definitely the toughest day I've had [at the Australian Open]," Agassi said.

"It's definitely the toughest day I've had [at the Australian Open]," Agassi said.

2004 Australian Open: Agassi Seeking Ecstasy

Winner of the Australian Open the last three times he’d played it (’00-’01, ’03), Andre Agassi arrived in Melbourne fit and confident. Reaching the semis without the loss of a set, he met the mercurial Marat Safin. Of the unseeded Safin’s five victories coming into the match, four had been versus Americans (Brian Vahaly, Todd Martin, James Blake, Andy Roddick). He earned a fifth against Agassi, winning 7-6 (6), 7-6 (6), 5-7, 1-6, 6-3. Said Agassi, “It’s definitely the toughest day I’ve had [at the Australian Open].” (Skilled as Safin was at beating Americans that fortnight, he’d lose the final to Roger Federer.)

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Roger Federer defeats Andy Roddick in four sets to win Wimbledon in 2004.

Roger Federer defeats Andy Roddick in four sets to win Wimbledon in 2004.

2004 Wimbledon: Roddick Chasing Roger

Though Andy Roddick had finished 2003 ranked No. 1, by February, Roger Federer had taken over the top spot. Seeded one and two at Wimbledon that year, the two smoothly advanced to the final. They split the first two sets. Roddick led the third 4-2, at which point the match was interrupted by rain for a second time. Coming to net more, Federer soon broke Roddick’s serve, won the third set in a tiebreaker 7-3, and in the fourth fought off six break points to close it out, 6-4. Said Roddick, "Roger I threw the kitchen sink at him, but he went to the bathroom and got a tub.”

The following year, he'd lose the final to Federer again, this time in a clinical 101 minutes.

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Roddick urges tennis players young and old to apply sunscreen.

Roddick urges tennis players young and old to apply sunscreen.

2005 US Open: A Surprising Run from Ginepri

This was one of the more improbable American men’s Slam semifinal runs of the Open Era. In 36 career majors, only once did Robby Ginepri advance past the fourth round. Five years after he’d lost to Roddick in the finals of the US Open junior tournament, this grinder found his best mix of fitness and form. Ranked 46th at the start of that year’s US Open, Ginepri was exceptionally impressive in earning five-set victories over Tommy Haas, Richard Gasquet and Guillermo Coria. Only the great Agassi could stop his run, that one too going the distance.

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In just two and a half hours, Federer outlasted Agassi to become the 2005 US Open champion.

In just two and a half hours, Federer outlasted Agassi to become the 2005 US Open champion.

2005 US Open: Agassi, Man of Destiny?

By 2005, thirty-five-year-old Agassi had outlasted such rivals as Pete Sampras, Jim Courier and Michael Chang. In the quarterfinals, playing one of the greatest matches in US Open history, Agassi rallied from two sets down to beat James Blake in a fifth-set tiebreaker. Next came another five-set victory, this one over Ginepri. In the final versus Federer, Agassi was brilliant. With the match tied at one-set all, Agassi led 4-2. Was he destined to win the title for a third time? Federer found a higher gear, winning that set 7-6 (1) and the fourth, 6-1.

2006 US Open: Andy and Jimbo Try to Reel in Roger

Following a third-round loss at Wimbledon, Roddick sent out what he called “a Hail Mary” and found a man who’d never coached but knew all about winning big titles: Jimmy Connors. Roddick gained much from Connors’ intensity—and penchant for taking the ball on the rise. All worked magnificently at the US Open, particularly when Roddick took down 2001 champion Lleyton Hewitt in the quarters. But in the final, Roddick was once again stymied by Federer, 6-2, 4-6, 7-5, 6-1. “You throw enough against the wall, said Roddick, “something’s going to stick one of these times.”

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2009 Wimbledon: Heartbreak

Every tennis player has at least one match that got way. But few suffer such heartbreak in a Wimbledon final. Boosted by victories over 2002 Wimbledon champ Hewitt and crowd favorite Andy Murray, Roddick once again met Federer in the final. Roddick won the first set and took a 6-2 lead in the second-set tiebreaker: four chances for a massive two-set lead.

Alas, Federer won six straight points. But Roddick persisted, eventually taking it into a fifth. Again and again in the decider, Roddick held serve to remain in contention. But at 14-15, he was broken for the only time in the match. The score says it all: 5-7, 7-6 (6), 7-6 (5), 3-6, 16-14.

In addition to his four Slam runner-up efforts, Roddick reached five other major semis (’03, ’05, ’07, ‘09 Australian Open and ’03 Wimbledon). Following Wimbledon ’09, eight years would pass before another American man reached a Slam semi.

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Sam Querrey loses to Marin Cilic in the 2017 Wimbledon Semifinal 7-6, 4-6, 6-7, 5-7.

Sam Querrey loses to Marin Cilic in the 2017 Wimbledon Semifinal 7-6, 4-6, 6-7, 5-7.

2017 Wimbledon: Serve It Again, Sam

From the time he’d turned pro in his teens, Sam Querrey’s massive serve and powerful forehand made it seem likely he’d frequently fare well at Wimbledon. At 30, did Querrey advance to the final four at the All England Club. He did it quite impressively, with five-set victories over fellow big hitters Jo-Wilfried Tsonga and Kevin Anderson. Then came a magnificent quarterfinal effort, Querrey upsetting the titleholder, world No. 1 Andy Murray, 6-1 in the fifth. But in the end, like all American men at the majors since 2003, Querrey’s run ended, this one by Marin Cilic, 7-5 in the fourth.

2018 Wimbledon: An In-Form Isner

Like Querrey, John Isner had the assets to make many a Wimbledon memory. One unforgettable one came in 2010: a 70-68 fifth-set win over Nicholas Mahut. But prior to 2018, Isner had played Wimbledon nine times and never gone past the third round.

That year, Isner was razor sharp. In the semis versus Kevin Anderson, Isner played yet another epic. But after six hours and 36 minutes, Anderson emerged the victor, 7-6 (6), 6-7 (5), 6-7 (9), 6-4, 26-24. Along with the Mahut match, Isner’s two marathons are considered the tipping point for Wimbledon opting to play a tiebreaker in the decisive set.

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2022 US Open: Tiafoe Dazzles

Early in his career, at the 2017 US Open, Frances Tiafoe had shown his appetite for the limelight when he’d extended Federer to five sets. Five years later, over the course of three straight matches, a much-improved Tiafoe further electrified Arthur Ashe Stadium.

First, in the round of 16, a breakthrough four-set win over four-time US Open champion Rafael Nadal. Next, a tight straight-set victory versus No. 11 Andrey Rublev. In the semis, Tiafoe pushed eventual champ Carlos Alcaraz to the limit, narrowly losing 6-7 (6), 6-3, 6-1, 6-7 (5), 6-3. It was the kind of effort that gave hope of great things to come.

2023 Australian Open: Paul Makes Magic in Melbourne

Consider Tommy Paul a precocious late-bloomer. In 2015, he’d beaten Taylor Fritz to win the junior title at Roland Garros. But it had taken more than six years for Paul to crack the Top 50 in the pros. In the summer of 2022, there’d been a career-best run to the round of 16 at Wimbledon.

Paul arrived at the Australian Open more aware of his eclectic skill set than ever, an array that took him through a five-setter versus Alejandro Davidovich Fokina in the second round and three more wins on his way to the semis. There, Paul came up against the Master of Melbourne, Novak Djokovic, losing in straight sets.