
Novak Djokovic boasts an incredible record at Grand Slam tournaments. He has won the most out of any player with 24, along with the most Australian Open titles with 10. Going into his 18th event at Flushing Meadows, the Serbian is targeting title number five.
He has made a positive start to the tournament, dumping out Learner Tien in straight sets before coming back from a set deficit to knock out qualifier Zachery Svajda. He will face Cameron Norrie in the third round at the US Open.
Unfortunately for Djokovic, that player represents Great Britain. If it were an American, like his earlier two opponents, then statistically, he would have had a better chance of making it through. The 38-year-old has faced Americans 43 times in major matches, only losing in three of them - Paul Goldstein, Andy Roddick, and Sam Querrey.
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Paul Goldstein
Possibly the least known out of the three players to beat Djokovic, Goldstein began his career back in 1998 after having a promising young career. He never broke out onto the main stage in tennis, reaching a peak ranking of 58 in singles and 40 in doubles. He made five ATP doubles finals, but lost every one. Four of them were with Jim Thomas, who is now a politician. The other one, he partnered with Robert Kendrick. Adding to that, he also made a semi-final with Thomas at Flushing Meadows in 2005, but were defeated by the eventual champions. A year later, he made the quarters, the same year he faced up against a future legend of the sport.
An 18-year-old Djokovic would play his second tournament in Melbourne, the place where he would taste so much success. He was looking to get his first win down under, but could not find away past the American, who won his first Australian Open match since 2001. It would also prove to be his last in Australia and penultimate for his career. Goldstein won the tie 6–2, 1–6, 6–3, 6–2.
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Andy Roddick
Djokovic would go three years without facing defeat to another American in a Grand Slam event. When it eventually came to former world number one Andy Roddick, it would prove to be a shock with Djokovic having won the title the year before. This had matched Roddick's tally of Grand Slams, with him winning the US Open back in 2003, utilising his blistering serve. He remains the last US Grand Slam champion.
He had since made four finals, three at WImbledon and one in New York, bu succumbed to defeat in all of them, amusingly all of them to Roger Federer.

Andy Roddick
By the time he matched Djokovic in the 2009 Australian Open semi-final, the Serb was touted as the favourite. Despite this, Roddick came back from losing the first set in a tiebreaker to breeze through the second and third sets, all before the then 21-year-old retired due to heat exhaustion and physical discomfort. The American would lose in the semi-final - to Federer. Djokovic would get his revenge in Roddick's final professional match, slaughtering him 6–2, 6–1, 6–2 in the US Open third round.
Sam Querrey
From 2010 to the current day, Djokovic's record at Wimbledon has been borderline perfection. He has reached the final ten times, winning seven of them, and failing to reach the quarter-finals once. That one time came to his third and final defeat from an American in a major match.
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Querrey was never hyped up as much as some of his fellow countrymen, but he did put his name on the map after a seismic upset in 2016 at Wimbledon. Previously at Grand Slams, his best result was in the fourth round at Wimbledon and the US Open back in 2009 and 2010, respectively, but he failed to kick on. That was until he met the world number one at Wimbledon.
Djokovic, the two-time reigning champion, came into it as the overwhelming favourite. On the other hand, Querrey defied the odds by sweeping aside the best player in the world in a seismic shock, winning 7–6(6), 6–1, 3–6, 7–6(5). It would prove to be one of the biggest upsets in 2016. The American would reach the quarter-finals before going one better the next year, knocking out reigning champion Andy Murray with a stunning burst at the end of the match before being pegged back by Marin Cilic in the semi-finals.

Sam Querrey
He reached a highest rank of 11th in the world in 2018, and made one more eye-catching run at Wimbledon in 2019, losing out to Rafael Nadal, who lost to Federer, who lost to Djokovic in a thrilling final. He is now a professional pickleball player.
Since his defeat in 2016, Djokovic has beaten every American who dared to challenge him on a Grand Slam court. He has a stunning 40-3 record against the Yanks, recently adding two new additions to the list at Flushing Meadows. If results go this way, his next American opponent would be Frances Tiafoe in the quarter-finals.
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Lucas MichaelTennis Journalist
Lucas Michael is a tennis journalist based in Cambridge, UK, specializing in comprehensive coverage of the ATP and WTA tours. For the past 1.5 years, he has been a core contributor to TennisUpToDate, where he has authored more than 3,000 data-driven match reports, deep-dive analysis pieces, and engaging liveblogs.
Lucas pairs real-time statistical analysis with on-the-ground reporting, frequently traveling to tournaments to cover the action firsthand from the press box and player press conferences. This blend of advanced metrics and direct access allows him to provide sharp context regarding player form, tactical trends, and breaking tour developments.
He holds a BA (Hons) in Sports Journalism. Grounded in core journalistic ethics, Lucas places a strict emphasis on meticulous sourcing, editorial accuracy, and a commitment to updating live content swiftly as verified information emerges.
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mandoist09-11-2026 - Ironically, Martina became a U.S. Citizen about the same time as the Orange Convicted Felon & Abuser was just beginning on his road to losing all Daddy's Millions!!
mandoist09-11-2026 - "Another fresh start is in the cards." Thanks for the Humor!! I'm guessing this is the minimum one can do to keep all your sponsors hanging-on in perpetuity?
mandoist09-11-2026 - Vukov is doing this to Lena... AGAIN!!!!! WTA's autonomous collective should be dismantled for allowing Vukov to re-emerge from his hand-slapping suspension. Just ask WTA employees how that's been going lately as they witness his continued verbal abuses. Women's Pro Tennis should start over.
mandoist08-11-2026 - Can't help but suspect Vukov is back to his old self again. Thank you, WTA. Perhaps you can give them a "Battling Couple of the Year Award 2026" ??
mandoist08-11-2026 - Wtf? Why is there no reason? And what about the men's?Bel08-11-2026
- One step by another step -- WTA continues to 'lose the plot'. Too many hi-tech microphones being installed at most venues!!! Remove them (especially those along the hallways, sidewalks, and pathways throughout the venues. Not to mention (most of all) remove the mic's from the Players/Coaches Box.
mandoist06-11-2026 - Enough of her bullshit. Go marry someone.
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