Wimbledon Gentlemen’s Singles Roundtable Predictions: Champion, Dark Horse, and Early Exit

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Ahead of Wimbledon, the world’s most prestigious tennis tournament, five Last Word On Tennis writers –Vithun Illankovan, Anurag Sahay, Damian Kust, Andrew Watson and Jakub Bobro – made their Wimbledon Gentlemen’s Singles predictions. We will also have a separate roundtable for the women’s singles.

Champion – Who will win Wimbledon? 

Vithun[1] Novak Djokovic (SRB)

After the French Open, we have learned that the ATP Tour is Novak Djokovic and then everyone else. In my opinion, I believe Wimbledon has been Djokovic’s best chance of winning a Grand Slam each year for the past few years as well as going forward. With many of his rivals likely due sub-par performances (see my early exit analysis), that couldn’t be truer this year. In fact, if Djokovic were not to win Wimbledon this year, I think it would be arguably his biggest missed opportunity to win a Grand Slam.

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Anurag: [3] Stefanos Tsitsipas (GRE)

Make no mistake, the third seed has been domineering this year with 39 match wins, including two ATP level tournament wins. Despite missing out on Wimbledon warm-ups the last fortnight, he will be brimming with confidence from deep runs at the French Open and Australian Open. He might not have a grass profile to boast about, much less at Wimbledon, but he is a much better player since he last competed at Wimbledon. If his potential SF opponent Djokovic drops guard in the opening set or two like he did on multiple occasions at the last French Open, I am inclined to believe Tsitsipas would be able to capitalize on the Serb’s vulnerability. The Greek just might end the “Big Four” monopoly at Wimbledon.

Damian: [1] Novak Djokovic (SRB)

In my view, it’s about a 50/50 between Djokovic and the rest of the field. There are some strong contenders like Matteo Berrettini, Roger Federer, or Daniil Medvedev (the last two under a bit of a question mark), but they were all placed in the other half of the draw. Grass in week one could lead to some upsets early but I don’t think Kevin Anderson is healthy enough to cause Djokovic a lot of trouble if they meet in the second round.

Andrew: [1] Novak Djokovic (SRB)

Is it possible to pick another name? I was thinking to myself whether I would take Djokovic or the entire rest of the draw, and I think I would still take the Serbian under those circumstances. It wouldn’t necessarily be a shock because he just won Queens but I am going to pick Matteo Berrettini to face him in the final. I can’t see a way in which Djokovic loses in his half of the draw.

Jakub: [1] Novak Djokovic (SRB)

Going for the obvious pick here, taking the five-time champion who is on-track for a Golden Slam in 2021. With Murray and Federer fading while the younger generation is yet to emerge on grass, Djokovic is the only logical choice. Unless the Serb will be hampered by injuries, it is nigh on impossible trying to imagine someone else taking the title.

Dark Horse – Who will go furthest in the draw, relative to their seeding (or ranking)?

Vithun: [7] Matteo Berrettini (ITA)

The seventh seed has never reached a Grand Slam final before but I believe he will finally achieve that milestone at Wimbledon this year. Having reached his first Masters 1000 final in Madrid earlier this year as well as just winning the biggest title of his career on the grass at Queens (only dropping one set along the way), 2021 has been a season of milestones for the Italian. In addition, given that I expect many of the top seeds to fall early, I predict that Berrettini will only need to beat one Top 10 player to reach the final and you don’t get many opportunities like that given the strength and depth of men’s tennis.

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Anurag: Lorenzo Musetti (ITA)

I would pick the talented Italian. He has not played a single match on grass this season, but has been handed a lenient draw up until the 4th round where he could run into Medvedev. Grass is certainly not his forte, but he probably won’t take long before adapting to the surface. With the all-round skills he possesses, I see Musetti reaching the 4th round if not any further than that.

Damian: [27] Reilly Opelka (USA)

The former Wimbledon champion in juniors had a good run here last time the event was held. The high seeds in his section (Denis Shapovalov and Roberto Bautista Agut) aren’t the strongest and if his serve’s firing, he could take out just about anyone. Beating Bautista Agut could be too much of an ask but if Opelka was to do it, he’d become my favorite to go to the quarters.

Andrew: Arthur Rinderknech (FRA)

The Frenchman looked increasingly comfortable on the grass during qualifying and despite a potential meeting with Andy Murray in round two he could reach at least round three and cause some headaches for many players. The previously mentioned Matteo Berrettini I have reaching two rounds further than his seeding and playing the final, everyone else I liked has a difficult draw. Cam Norrie and Jack Draper for the home team have Federer and Djokovic early, but Norrie could get the better of Federer in the third round.

Jakub: [32] Marin Cilic (CRO)

The 2017 Wimbledon finalist comes into the tournament on great form, taking the title in Stuttgart and making the quarterfinals at Queen’s Club. The first two rounds were kind to Cilic, opening against Salvatore Caruso and facing a qualifier in Trungelliti or Bonzi in the second round. Next is when the challenge begins for Cilic, potentially facing second seed Daniil Medvedev, though the Russian has never made it past the third round. If Cilic gets past Medvedev, I could see him reaching the quarterfinals at Wimbledon as his potential fourth-round opponents include out-of-form seeds (Hurkacz, Dimitrov) or unproven youngsters (Musetti, Ruusuvuori).

Early Exit – Who will suffer the earliest exit, relative to their seeding (or ranking)?

Vithun: [2] Daniil Medvedev (RUS)

Of the four Grand Slams, Wimbledon is the most unpredictable for the men (excluding the champion that is!). Daniil Medvedev, Alexander Zverev and Stefanos Tsitsipas are all due early exits (relative to their seeding). Medvedev and Zverev have never made three consecutive Grand Slam quarter-finals before. Tsitsipas has never made four consecutive Grand Slam quarter-finals before and seven of the last eight first-time Grand Slam finalists have failed to reach the quarter-finals at the following Grand Slam.

Of these players, Medvedev is seeded highest, but expect him to lose earliest (3rd Round, four rounds earlier than his seeding). Whilst Medvedev did just win his first grass-court title in Mallorca, his opening match is against Jan-Lennard Struff who took out his Russian Top 10 compatriot Andrey Rublev in the French Open first round. If he gets past that, he will likely play Marin Cilic in the third round who reached the 2017 Wimbledon final and also won a 2021 grass-court title in Stuttgart. With the bad omen I mentioned, it is unlikely Medvedev will get through both of these matches.

However, the most likely opening round exit for a Top 16 seed will be 14th seed Hubert Hurkacz. He has suffered the fate which we have seen countless times in the WTA but rarely in the ATP – an unheralded player having a huge result (winning the Miami Masters) and then faltering under the pressure of being a high-ranked player (six-match losing streak) as they achieved peak success quicker than their ability suggested. An opening match against the talented Lorenzo Musetti who reached the 4th Round of the French Open (and took two sets of Djokovic) is unlikely to change his fortunes.

Anurag: [9] Diego Schwartzman (ARG)

Who else would that be at Wimbledon? The Argentine has not got much of a footing on grass. To add to that, not only does he underperform in pressure situations, Schwartzman lacks a necessary weapon on grass – a dominant serve. The draw may not help his chances either. Even if he brings all he has got to the court, it is a tall order for him. Paire is in poor form. So, I am looking at a second round exit, if not earlier.

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Damian: [9] Diego Schwartzman (ARG)

As usual, it’s a matter of which Benoit Paire comes out to play him in the opening round. However, it’s statistically the Frenchman’s best slam and his all-or-nothing game usually works out quite well on the grass. The draw eases up a bit later but I still wouldn’t expect any deep run from the Argentinian on this particular surface. Daniil Medvedev’s another one that could be in trouble with Jan-Lennard Struff in his opener and then potentially Marin Cilic in the third round. He’s a much, much stronger grass-courter than Schwartzman though.

Damian: [8] Roberto Bautista Agut (ESP)

I think there are a lot of seeds in trouble in round one. Daniil Medvedev would not have enjoyed seeing Jan-Lennard Struff’s name come out for him in the opener. Shapovalov might struggle against the experienced Philipp Kohlschreiber but I am picking RBA to depart against the hardy John Millman.

Jakub: [13] Gael Monfils (FRA)

Went for an easy pick here if we’re looking at underperforming compared to seeding with Monfils. The Frenchman is seeded 13th, thus seeded for the fourth round which he has only reached at Wimbledon once. The 34-year-old has been struggling immensely since the pandemic, his record being 2-12 since the restart. Grass is his worst surface, Wimbledon his worst slam, and he faces qualifier Christopher O’Connell, who won three tight matches to qualify. A first-round exit for Monfils is to be expected.

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