Ahead of the 2020 Tokyo Olympics (taking place in 2021 due to the COVID-19 pandemic), five Last Word On Tennis writers-–Vithun Illankovan, Damian Kust, Anurag Sahay, Steen Kirby and Jakub Bobro––make their Men’s Singles predictions. We will also have a separate roundtable for the Women’s Singles.
Tokyo Olympics Men’s Roundtable Predictions
Champion – Who will win Gold at Tokyo 2020?
Vithun:  Daniil Medvedev (ROC)
When we did our Wimbledon roundtable predictions I said the ATP Tour is Novak Djokovic and then everyone else, and the Serbian proceeded to comfortably win his 20th Grand Slam title. Therefore, it may seem strange for me to not to pick him as my Gold medallist but there are some bad omens which I think may stop him achieving the Calendar Golden Grand Slam.
Firstly, there is the pressure. When Serena Williams was one tournament away from achieving the Calendar Grand Slam in 2015, we eventually saw her crumble in a loss to Roberta Vinci in what was arguably the biggest upset in tennis history. Whilst present-day Djokovic is much more stronger mentally (compared to the Serena of the last decade), the pressure of trying to achieve a historic and unprecedented feat (in men’s tennis) could overwhelm him, particularly as he has never won Olympic gold.
The reason why I believe Rafael Nadal is the only one out of the “Big 3” to have an Olympic Singles Gold is because he won it before completing the Career Grand Slam so it wasn’t the sole elusive big title for him. Roger Federer put in a below-par performance in the London 2012 final, partly due to fatigue but also from the pressure of knowing it was the one big title he had yet to win. Also, unlike Grand Slams, you cannot just return in 12 months time to make amends. Unfortunately I can see the same fate for Djokovic in Tokyo.
In addition, Djokovic is carrying a long (18-match) win streak, which is never ideal when entering a big tournament. When Nadal did the Roland Garros-Wimbledon double in 2008, he smartly lost a match (to Djokovic) before the Olympics so he wasn’t carrying that unnecessary additional pressure. He ended up winning the Gold, beating the Serbian en route. Djokovic has been the victim of maintaining long win-streaks in big events before (2011 French Open and 2020 US Open come to mind, both events I predicted he wouldn’t win for this sole reason) and really think he should have entered a tournament after Wimbledon and lost a match to take some pressure off himself.
For these reasons, I see Djokovic making the final but then putting in a performance well below his best and coming up short. The question is then–who would beat him? I have gone for Medvedev. The Russian is the next most credible hard-court player on tour right now, and has reached two Grand Slam finals on the surface, including the Australian Open this year. In addition, this Olympics the final is also only a Best of 3 sets format, which favors the Russian–he has a 2-1 record against Djokovic in matches with this format on hard courts. As a result, I am picking Medvedev to with Olympic Gold in Tokyo!
Boring, but let’s be honest, I’m probably going to pick Djokovic for any tournament left this year. The rest of the “Big Four” already have a Gold Medal at the Olympics (in either singles or doubles) and it looks like the Serbian really wants to join them in that regard too. Being so hungry for something can often backfire, but at least in 2021, Djokovic has been winning all the events he wanted the most. Plus, there’s no del Potro in the draw this time around.
Anurag:  Novak Djokovic (SRB)
Novak Djokovic is a clear favorite but his best result was a Bronze way back in 2008. Daniil Medvedev is very dangerous on hard-courts and he is coming off two great seasons back-to-back. The all-star Russian contingent in Tokyo might prove to be a step forward in the Russian tennis movement. As much as I trust the Russian’s hard-court expertise to take him through, it only makes sense to go with the man of the moment–Novak Djokovic–in his quest for the first Gold medal in what will likely be his last appearance at the Games. Not to mention he has got a draw much aligned with his seeding.
Steen:  Novak Djokovic (SRB)
The World #1 is simply the best in class tennis player in the world right now. This draw is not as challenging as a typical Grand Slam and it’s hard to see anyone being able to stop Djokovic from winning the Gold Medal. He remains hungry for more after achieving so much.
Jakub:  Novak Djokovic (SRB)
Isn’t it obvious? Novak Djokovic may not be the most famous or the most popular of the “Big Three,” but he is certainly on track to end up being the most successful. Three-fifths of the way to a Golden Slam already, the World No. 1 is showing no signs of slowing down. Sure, he has Musetti waiting in the third round or Rublev in the quarterfinals, but I would be shocked if any hurdle in Djokovic’s way causes him to stumble.
Dark Horse – Who will go furthest in the draw, relative to their seeding (or ranking)?
Vithun:  Karen Khachanov (ROC)
The Russian just made the quarterfinals at Wimbledon and is in a nice section of the draw. I see no reason why he can’t repeat a quarterfinal result at the Olympics too. I also expect his compatriot Aslan Karatsev and fellow Wimbledon quarterfinalist Felix Auger-Aliassime to reach the final eight in Tokyo, despite all only being seeded for the last 16.
Damian:  Diego Schwartzman (ARG)
Very nice draw where he’s bound to face Juan Pablo Varillas in the opening round, then Tomas Machac or Joao Sousa. Issues should start with Karen Khachanov later, but the reported conditions should suit his baseline game, and there’s not many players that will be able to outlast the Argentinian in the extreme heat. A quarterfinal/semifinal run isn’t out of the question at all.
Anurag: Marin Cilic (CRO)
Fabio Fognini is a strong contender on the surface, but he couldn’t make a deep run in the last edition in Rio. He has also been inconsistent this year. Hubert Hurkacz, Kei Nishikori, and Felix Auger-Aliassime are all tempting dark horses. But I will go with Cilic who is a dependable dark horse and is unseeded. His recent performances make it hard not to consider him as a potential troublemaker to the top seeds. The Croat has a lenient draw up until the third round before he runs into either Andy Muray or Felix-Auger Aliassime. If he passes the test, he will likely be in for a stern test against Medvedev. A third round or quarterfinal exit would still make him a Dark Horse. Cilic into the 3rd Round.
Steen:  Hubert Hurkacz (POL)
When Hurkacz is playing well, his serve is nearly unbreakable, he had a great Wimbledon and also won Miami this year on hard courts. A run to the semifinals for a meeting with Djokovic would not come as a surprise, this is Alexander’s Zverev’s quarter of the draw and it is winnable for Hurkacz.
Jakub:  Karen Khachanov (ROC)
This is a pick that screams recency bias as Khachanov is fresh off a Wimbledon quarterfinal, but it is worth remembering that his start to the year on Australian hard courts was not horrible, taking narrow losses to Sinner and Berrettini. The Russian has a good draw, opening against a struggling Yoshihito Nishioka and Diego Schwartzman being the other seed in his section. The high seed in the next section is Stefanos Tsitsipas who is 1-2 since the French Open, so Khachanov has a solid route to the semifinals.
Early Exit – Who will suffer the earliest exit, relative to their seeding (or ranking)?
Vithun: Nikoloz Basilashvili (GEO)
For some reason the Georgian is usually abysmal outside of Germany. In his last ten tournaments outside of Germany he has a 3-10 record. Unfortunately for him the Olympics are happening in Japan and so despite being ranked 48 places higher than his first round opponent Roberto Carballes Baena, I do not expect him to win that match. I also expect an early exit for 10th seed Gael Monfils. The entertaining Frenchman has not won back-to-back matches since the resumption of the tour last year after the disruption from the COVID-19 pandemic and so anything beyond the 2nd round for him would be a shock.
Damian:  Gael Monfils (FRA)
Still in dreadful form and Ilya Ivashka is having by far the best season of his career, going deep at Wimbledon and forcing Nadal and Federer to really work to beat him. The Frenchman’s second-round isn’t as tough, but he even if he scrapes through, Andrey Rublev/Kei Nishikori should be the end of the road. Hubert Hurkacz is playing Marton Fucsovics in his opener, but after that, his draw eases up. Same for the aforementioned Rublev, but you can never count out Nishikori at home and playing for Japan.
Anurag:  Gael Monfils (FRA)
Gael Monfils as an option would have sounded out of place 5 years ago. But he is on a downward spiral now, with only occasional wins here and there. A dry 2021 season does not help his prospects either. A deep run is therefore probably a big ask for the Frenchman. If Ivashka doesn’t take him out in Round 1, I predict a Round 3 exit at the hands of either Nishikori or Rublev.
Steen:  Stefanos Tsitsipas (GRE)
Tsitsipas has plenty of talent, but his recent form since losing the Roland Garros final to Djokovic has lagged. With his game looking a bit worse for wear an underwhelming Olympic showing would not come as a surprise.
Jakub:  Hubert Hurkacz (POL)
Hurkacz has had a roller coaster of a year, starting with a title in Delray Beach but then having a mediocre 4-5 run including a first round exit at Australian Open until his Miami title. After it, the Pole went 1-6 until Wimbledon where he reached the semifinals out of nowhere. Hurkacz’s season has had a pattern of high peaks and prolonged valleys, so it is possible that he will arrive at the Olympics out of form. Couple that with a tricky opponent in Marton Fucsovics who is also coming off of a strong Wimbledon run and also leads the head-to-head over Hurkacz 2-0, and we might see the 24-year-old exit the Olympics in the first round.
Main Photo from Getty.