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Men's Wimbledon Preview: Can anyone derail Novak Djokovic's quest for a calendar-year Grand Slam?

The man who came closest to knocking off Nole at the last edition of Wimbledon, Roger Federer, might still have the best chance.

BySteve Tignor

Published Jun 26, 2021

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WATCH: What's on the line at Wimbledon for Novak Djokovic?

After the long buildup to Roland Garros comes the mad scramble to Wimbledon, which was made even madder this year because it lasted two weeks instead of three. By the time the players get to Paris, we have a pretty idea of who is in form and who isn’t. At Wimbledon, it’s anyone’s guess.

One thing we do know is that Novak Djokovic is the top seed, the defending champion, and the favorite. Is there anyone out there who might derail his quest for the calendar-year Grand Slam?

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First Quarter

Is there any reason for Djokovic’s opponents, or the fans who aren’t in his camp, to believe he might not win his 20th major title two weeks from now? His history does offer a morsel: The only other time he won the French Open, in 2016, was also the only time he has lost in the first week at Wimbledon since 2008. That year big-serving Sam Querrey upset Djokovic in the third round. At first glance, a repeat of that shocker seems unlikely.

Djokovic will start against Jack Draper, a 19-year-old British wild card ranked 250th. Upset-wise, that’s not promising, but it should be noted that Draper is a lefty, he’ll have the crowd behind him, and he beat Jannik Sinner and Alexander Bublik at Queen’s Club. So it should at least make for a lively way for the Championships to return on Centre Court. Djokovic could play Kevin Anderson in the second round, in a repeat of their 2018 final; Alexander Davidovich Fokina in the third round; ever-unpredictable Gael Monfis in the fourth round; and No. 5 seed Andrey Rublev in the quarters. Rublev is the cream of that crop, but just making it to the quarters would be an achievement for him; he has never been out of the second round at Wimbledon.

First-round matches to watch:

Sinner vs. Marton Fucsovics
Benoit Paire vs. Diego Schwartzman

Semifinalist: Djokovic

The only other time Djokovic won the French Open, in 2016, was also the only time he has lost in the first week at Wimbledon since 2008.

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Second Quarter

When it comes to Stefanos Tsitsipas and his status at the moment, questions abound. Will his Roland Garros experience leave him feeling more confident about his ability to go deep at Slams—or deflated by the fact that he couldn’t close the door in the final? After an arduous and successful clay season, is he ready to make the transition to grass? His career record at Wimbledon is just 3-3, and he hasn’t played any tune-up events this year. Tsitsipas will want to be ready right away. In the first round he’ll play Frances Tiafoe, who recently won a grass-court Challenger event in Nottingham.

After that, though, things may open up a bit for Tsitsipas. The first seed he could face is 25th-ranked Karen Khachanov, and the second-highest seed in this section is Roberto Bautista Agut.

Also here: Andy Murray. The two-time champion and sentimental favorite will start against 24th-seeded Nikoloz Basilashvili.

First-round matches to watch:

Tsitsipas vs. Tiafoe
Murray vs. Basilashvili
Denis Shapovalov vs. Philipp Kohlschreiber
Alex De Minaur vs. Sebastian Korda
Dan Evans vs. Feliciano Lopez
Reilly Opelka vs. Dominic Koepfer

Semifinalist: Tsitsipas

2021 Wimbledon: Featured first-round match-ups

Ranked 61st but always a threat at SW19, Nick Kyrgios—whose last Wimbledon match was a four-set loss to Rafael Nadal—will face talented youngster Ugo Humbert.

Roger Federer returns to the All England Club seeking his ninth Wimbledon title—and trying to wipe away the sting of the 2019 final. After pulling out of Roland Garros as a precautionary measure, the 39-year-old will face Adrian Mannarino in the first round. (He's also away from Djokovic's half of the draw.)

Iga Swiatek has never won a main-draw match at Wimbledon. She'll get another chance when she faces the crafty Hsieh-Su Wei.

If Novak Djokovic is to win his 20th Grand Slam title—and continue on his quest for a calendar-year Slam—he'll first need to get by 19-year-old Brit Jack Draper.

Sebastian Korda will play in the main draw for the first time, with the 20-year-old American drawing Alex de Minaur.

Daniil Medvedev said he didn't like clay, but he did pretty well at Roland Garros. How about grass? He's currently doing well in Mallorca; at Wimbledon, he'll face Jan-Lennard Struff in the first round.

Coco Gauff's last first-round match at Wimbledon was her coming-out party, having defeated Venus Williams. This year's opening-rounder won't be as star-studded, but it will still receive plenty of attention, as Britain's Fran Jones opposes the talented teen.

Sloane Stephens got one of the most difficult draws an unseeded player could ask for at the All England Club: a date with two-time champion Petra Kvitova.

For all Andreescu has already achieved, she's never won a main-draw match at Wimbledon. The 21-year-old Canadian will be asked to do plenty against veteran Alize Cornet.

Serena Williams has Grand Slam singles title No. 24 on her mind; before that, though, she'll only be thinking about her first-round opponent, Aliaksandra Sasnovich.

Andy Murray needed a wild card to get into Wimbledon, and his last memorable moment at the tournament came when he played mixed doubles with Serena. But the beloved two-time champion will try and rekindle great Centre Court memories when he faces Nikoloz Basilashvili.

French Open champion Barbora Krejcikova is 1-3 at Wimbledon—all in qualifying matches. Her first-rounder against 18-year-old Dane Clara Tauson won't be an easy introduction to the main draw.

Like Murray, iconic former champion Venus Williams needed a wild card into Wimbledon. But Mihaela Buzarnescu will try to make the most of her opportunity, as well.

Fresh off a runner-up finish at the French Open, Stefanos Tsitsipas will try to take the final step towards his first major at Wimbledon. In the first round, though, he gets a tough test in Frances Tiafoe.

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Third Quarter

Matteo Berrettini and Alexander Zverev are the top two seeds here, and considering that they’re not in Djokovic’s half, each would seem to have a chance to reach the final. Zverev is coming off a semifinal run at Roland Garros, and Berrettini a title at Queen’s. When they met on clay in the Madrid final a few weeks ago, Zverev had the advantage; on grass, that might shift to Berrettini.

But let’s not get ahead of ourselves—neither of them have been past the fourth round at Wimbledon before. Of the two, Berrettini seems to have a more difficult path; he might have to deal with John Isner in the third round, and either Aslan Karatsev or Casper Ruud in the round of 16. The seeds in Zverev’s half are Taylor Fritz, Ugo Humbert and Felix Auger-Aliassime. But there is one wild card lurking there: Nick Kyrgios, who will play Humbert in the first round. The last time they met, at the Australian Open, Kyrgios saved a match point and won in five sets. That was also the last match Kyrgios won against anyone. How he’ll look after five months away is tough to say, but no seeds are going to want to face him.

First-round matches to watch:

Isner vs. Yoshihito Nishioka
Kyrgios vs. Humbert
Kei Nishikori vs. Alexei Popyrin
Jo-Wilfried Tsonga vs. Mikael Ymer
Taylor Fritz vs. Brandon Nakashima

Semifinalist: Berrettini

Roger Federer held two championship points the last time he played Wimbledon.

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Fourth Quarter

We know about Daniil Medvedev’s mixed feelings about clay. What about grass? He hasn’t exactly lit up the courts at Wimbledon, where he is just 5-3 and has never been past the third round. But instead of waiting for the Slam itself to try to play his best, the way he did in Paris, Medvedev has made the final this week in Mallorca on grass. He has a tough first round at Wimbledon against Jan-Lennard Struff, but provided he survives that, Medvedev should be a factor.

There will be an even bigger factor in this section, though: Roger Federer. The eight-time champion wasn’t sharp in Halle, but this is the fortnight he has been waiting two years for, and no one knows his way around the show-court grass at Wimbledon like him. Even though he’s 39, defeating him over best-of-five sets will require a major mental effort. Federer will start against Adrian Mannarino, a player he has beaten in all six of their meetings. His first test could come against Cam Norrie, a British lefty who reached the final last week at Queen’s. If Federer makes it through that, and sees a few seeds falling around him, he might just start to believe the impossible is possible again.

First-round matches to watch:

Federer vs. Mannarino
Medvedev vs. Struff
Hubert Hurkacz vs. Lorenzo Musetti
Pablo Carreño Busta vs. Sam Querrey
Tommy Paul vs. Carlos Alcaraz

Semifinalist: Federer

Even though he’s 39, defeating Federer over best-of-five sets will require a major mental effort.

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