The five players who could upset Novak Djokovic at Wimbledon

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Every tournament has favorites. Rarely does a tennis tournament have someone who’s favored against the rest of the field combined. Then again, rarely is a player as dominant as Novak Djokovic has been at Wimbledon.

Djokovic has won 31 matches in a row at Wimbledon, and he’s won 43 of his last 45 on grass. Neither of the two players who beat him — a retired Tomas Berdych or an injured Marin Cilic — entered the Wimbledon field this year. Djokovic began the quest for his eighth Wimbledon crown with betting odds of -175, per Caesars. Those are implied title odds of 64% for him and 36% for the other 127 players in the field. Three rounds into the tournament, his odds are up to -200 (equivalent to 67%). And good luck finding someone confidently willing to bet against him.

Still, there are four rounds to go, and, well, this is a tennis tournament. Strange things happen! Djokovic lost to Sam Querrey at Wimbledon in 2016 and to Berdych in both 2010 and 2017. He may be the safest bet in the sport, but there are no 100% guarantees.

With that in mind, let’s talk about the obstacles he still faces in the rounds to come. First, following his straight-set win over Stan Wawrinka on Friday, here’s Djokovic’s likely remaining Wimbledon path:

Fourth round: No. 17 Hubert Hurkacz

Quarterfinals: No. 7 Andrey Rublev (64% chance of reaching the round, per Tennis Abstract) or No. 23 Alexander Bublik (36%)

Semifinals: No. 8 Jannik Sinner (73%), No. 26 Denis Shapovalov (15%), Roman Safiullin (10%), Daniel Elahi Glaan (3%)

Finals: No. 1 Carlos Alcaraz (37%), No. 3 Daniil Medvedev (23%), No. 5 Stefanos Tsitsipas (11%), Matteo Berrettini (6%), No. 10 Frances Tiafoe (6%), No. 6 Holger Rune (5%), No. 16 Tommy Paul (3%), nine others under 3%

Who are the five players with the best chance of pulling a major upset, and handing Djokovic his first Wimbledon loss since 2018?

1. Carlos Alcaraz

When he would play Djokovic: Finals

Obviously we start with Alcaraz. The 20-year-old is the top-ranked player in the world, and he won one of their two head-to-head matches. He’s still learning how to play on grass — his second-round win over Alexandre Muller was just his 13th senior-level match on the surface – but he’s won 10 of his last 11 grass matches and all seven in 2023. He learns quickly.

Alcaraz has plenty of hurdles remaining to get to what would be our first Djokovic-Alcaraz final. Either Alexander Zverev or 2021 finalist Berrettini would await in the fourth round, followed by maybe either Rune or Tiafoe in the quarterfinals and either Medvedev or Tsitsipas in the semis. That’s a lot. But if he has polished his form enough to survive those challenges, and he is better able to relax in the run-up to meeting Djokovic (he suffered stress-related cramps in their French Open semifinal battle), he could be ready to take down the best ever in a best-of-five.

2. Jannik Sinner

When he would play Djokovic: Semifinals

Something clicked for Sinner at Wimbledon last year. He entered the 2022 Championships just 2-6 all-time on grass, but he took down Wawrinka, John Isner and Alcaraz on the way to the quarterfinals, where he also took the first two sets against Djokovic. As has become customary, however, it was one-way traffic from there — 6-3, 6-2, 6-2 for Djokovic.

Sinner has looked mostly outstanding in the first week, dropping a set against Quentin Halys but winning six others by 6-2 or worse. Still only 20, he’s a brilliant ball-striker, his movement is good and if not for Alcaraz’s incredible rise over the last two years, we’d be talking a lot more about Sinner’s enormous potential. He’s also in the friendliest quarter by far. His odds of reaching the semis are high (73%, according to Tennis Abstract), and he knows he can compete on this surface. But there’s confidence, and there’s “winning three sets against Novak Djokovic” confidence. We only know that Sinner has the former.

3. Hubert Hurkacz

When he plays Djokovic: Fourth round

It’s been an up-and-down year for Hurkacz in 2023. The 26-year-old has reached a final and three semifinals (including one on grass in Stuttgart), but he’s also lost six of seven against top-20 opponents. That lone win, however, came on Friday at Wimbledon, when he swept Lorenzo Musetti, 7-6, 6-4, 6-4, to advance to the fourth round.

The big-serving, 6-foot-5 Hurkacz seems like your prototypical grass-court star, and his record certainly backs that up. He took a set from Djokovic at Wimbledon in 2019, he beat Roger Federer on his way to the semis in 2021, and he’s won 16 of his last 20 on grass. While no one serves-and-volleys enough these days, he is capable of utilizing that old-fashioned strategy — something that gave Djokovic moments of discomfort against Jordan Thompson in the second round — more than most. And considering the way Djokovic tends to play himself into tournaments and improve with every round, playing him in the fourth round might be preferable to playing him late in the second week.

4. Daniil Medvedev

When he would play Djokovic: Final

At Slams, Djokovic is a combined 29-1 against the 23 other men remaining in the Wimbledon field. He’s dropped sets against quite a few of them, but only one has taken three sets against him in the same match: Medvedev, in the 2021 US Open final. He absolutely has to go on this list, then, even if grass isn’t his best surface.

He’s improving on grass, though. He’s won 19 of his last 25 on the surface, and he just avenged one of his recent losses with a straight-set win over grass specialist Adrian Mannarino. He prefers life far beyond the baseline, and his long, looping strokes can make quick adjustments to funky bounces hard. But he’s figuring it out, and he’s looked good in his first two matches. And if he makes it to the final against Djokovic, he will bring to the table one piece of knowledge no one else in this field has: the fact that he can, in fact, beat the guy across from him.

5. Frances Tiafoe

When he would play Djokovic: Final

The odds of Big Foe reaching the final and getting a shot at Djokovic at all aren’t great. In consecutive rounds, he might have to beat Grigor Dimitrov (a semifinalist in 2014), 6-seed Rune, Alcaraz and either Medvedev or Tsitsipas. You could make a strong case for Rublev (Djokovic’s likely quarterfinal opponent), Rune, Tsitsipas, Zverev or even a rounding-into-form Berrettini in this spot instead of Tiafoe.

So why go with the Maryland native? Because confidence is not an issue for a guy who beat Rafael Nadal at last year’s US Open (and stretched Alcaraz into five long sets two rounds later) and has won 11 of his last 13 matches on grass. Unless you’ve got a humongous serve, winning on grass requires high levels of both brawling and improvisation. He’s got those things in droves, and he seems more comfortable on the surface with every match he plays. He took a set from Djokovic at the Australian Open in 2021, too. No one on this list has amazing odds at beating Djokovic, but I would give Tiafoe a better chance than most.

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