Wimbledon 2021 men's semifinals - Does Denis Shapovalov have a chance against Novak Djokovic?

Djokovic not worried about chasing Federer milestones (3:25)

Roger Federer is knocked out of the Wimbledon tournament. Novak Djokovic advances to the semifinals and comments that he is not concerned with chasing any Roger Federer milestones. (3:25)

Novak Djokovic has been the heavy favorite to win it all at Wimbledon. And heading into the men's semifinals (Friday, 8 a.m. ET on ESPN, ESPN App), he is on the cusp of his 20th career Grand Slam singles title.

Can first-time Slam semifinalist Denis Shapovalov pull off the upset? And what should we expect in the other matchup between two more Slam semifinal first-timers Matteo Berrettini and Hubert Hurkacz?

Our tennis gurus break down what to watch for and make their predictions.

Shapovalov faces a big task in facing Djokovic. Which part(s) of his game can he utilize in trying to pull off an upset?

ESPN TV analyst Darren Cahill: Denis can be a disruptor with his ball-striking power. The way he played the final two sets of his quarterfinal match against Karen Khachanov is a good blueprint: hit hard with good margin until you get the right ball to attack, and then launch. Breaking open the court with his lefty forehand will open up opportunities, but it is taking care of his service games that will be key. Novak will place relentless pressure in his return games by limiting the free points Denis gets on serve. He has to keep that first serve percentage around the 65 mark, and using the forehand-body serve to jam Novak will be a decent play. He will need Novak to have an average day because, if Novak is close to his best, he is not losing to anyone.

ESPN tennis contributor Simon Cambers: Shapovalov has to serve well. His Achilles' heel is double faults. If he serves well and cuts out the double faults, he will give himself a genuine chance.

ESPN TV analyst Brad Gilbert: Shapstick has to have a great day on his serve and take a lot of chances with his forehand. Still, even if the Canadian is hot, it's a huge ask to beat Djoker on grass.

ESPN writer Tom Hamilton: Shapovalov has a wonderful backhand -- he winds it up and then explodes through the ball. Andy Murray found that hard to deal with in their third-round match. Shapovalov also needs to ensure he manages his serves well. Against Karen Khachanov, he won just 50% of points on his second serve and had 10 double faults.

ESPN writer D'Arcy Maine: Even if Shapovalov is playing his best tennis, this is still going to be a substantial challenge. There's a reason Djokovic has won all six of their previous meetings, after all. Still, as Shapovalov said multiple times Wednesday, "Anything is possible," and he's right. His lefty serve could do some damage, as it did against Khachanov, and even Djokovic acknowledged how tough it is to get opportunities during Shapovalov's service games. He will need to seize every chance there and continue to be mentally strong. After winning the first set Wednesday, Shapovalov lost the next two before fighting back for the win. He's going to need to have that same mindset, and then some, against Djokovic.

ESPN editor Kathleen Mcnamee: Every part of Shapovalov's play will need to be inch-perfect if he is to beat Djokovic, as their head-to-head record and Djokovic's general form at the moment shows the Serb has the upper hand. This will be particularly important with his service game, which he has utilized at points but has struggled with double faults.

ESPN TV analyst Rennae Stubbs: Shapovalov has to use his big game and big attitude. He should use his lefty serve into the forehand as much as possible, try and jam up Novak on that side on the return. He has such a great attitude that, I believe, he needs to use that and try to get the crowd on his side and try and get under the skin of Novak. Novak is so locked in right now that you have to take it to him and show as much intensity as possible, because sitting back and expecting errors will make for a really long (or short) day for the Canadian.

Yes, we've asked before, but if Djokovic continues his run and wins Wimbledon, where do you currently stand on the GOAT argument?

Cahill: A win at Wimbledon for Novak changes nothing, but feel free to ask me this question again if he wins Wimbledon and the US Open this year. He may end up being the greatest of this generation anyway, but a Grand Slam would basically forge it in stone.

Cambers: It's still too early to say. Djokovic would be in pole position, given his age and that he is still No. 1, but things can change, and the total number of Slams may not be the only relevant criteria.

Gilbert: For me, there's zero point discussing the GOAT now. Djoker will have quite a few more chances to win more Slams over the next couple of years, so we'll have no answers then.

Hamilton: It all depends on your own subjective criteria. If it's on Grand Slams alone, then Djokovic will likely emerge from this golden period in the sport with the most singles titles to his name. If it's aesthetics, then you may prefer Roger Federer or Rafael Nadal. Either way, this debate will run way beyond when the three greats retire. For most, it'll be Federer.

Maine: Even if Djokovic doesn't secure No. 20 this weekend, he undoubtedly will by the US Open, and that's why he's already moved into the top spot for me in the GOAT conversation. Federer and Nadal don't appear to be quite at the same level these days, while Djokovic is still very much in his prime. I don't think there's any question Djokovic will soon take over sole possession of the record, and I wouldn't be shocked if he catches Serena Williams' Open era record of 23.

Mcnamee: If you're basing the debate purely off Slam wins, then a Wimbledon title would certainly put him ahead of the others. However, having seen how the crowd loves Federer these last two weeks and the level he has achieved after such serious injuries, it feels too early to judge Djokovic's legacy.

Stubbs: There is no doubt in my mind Novak is going to win the calendar Grand Slam this year, as well as possibly doing what Steffi Graf did and add an Olympic gold medal to it. He is so dominant right now, it's going to take the match of someone's life to beat him, particularly over 5 sets; it's possible over three sets at the Olympics, but tough to do at the Grand Slam level. If he wins all four Slams in one year, that will finally put the lid on the GOAT argument. He has been so dominant over Roger and Rafa over the past decade, and once he passes them on the Slam count, there is no more argument.

What are the keys for Berrettini and Hurkacz in their clash?

Cahill: Hurkacz has done a remarkable job in his past two matches against two very different opponents. He has shown an ability to adapt his game plan. Against Berrettini, it will be different again, with massive power coming from the serve and forehand. He will zone in the backhand of Berrettini, but sometimes you have to play the strength to find the weaker side, and that is dangerous. Ultimately, Hurkacz will want to make Berrettini play backhand passing shots, especially on the big points. The cat-and-mouse game should be a fascinating watch.

Cambers: Holding your nerve when it matters will go a long way in deciding this semifinal, but in terms of shots, it's about the serve. If Berrettini serves well, he can take the match out of Hurkacz's hands. Hurkacz returned very well against Federer. He will need to do the same again.

Gilbert: This is a very open matchup between Hurk Locker and Berrettini. It comes down to who handles the occasion and opportunity, as they both have huge serves and both will want to dictate from the center of the court.

Hamilton: Hurkacz returned well against Federer, but needs to convert more of the break points he engineers (just five from 15 against the Swiss great). It'll be a battle of offense against defense. Berrettini serves big (he has 79 aces at Wimbledon) and is well-renowned for his powerful forehand. But, as Hurkacz has proven at Wimbledon, he can handle everything thrown at him.

Maine: Berrettini's serve has been a major weapon and he will need to continue to utilize that and his strong forehand. After winning the title at Queen's, he's on a 10-match winning streak and his current confidence and momentum may prove to be unstoppable.

Hurkacz just won the biggest match of his life against Federer, never letting himself get intimidated by the moment. He's going to need to bring that same level of calmness into the semifinal and not get swept up in what's at stake now. Both players know this is an incredible opportunity, so it might come down to who can handle their nerves and the pressure better.

Mcnamee: Beating Federer in front of an adoring crowd will have been a massive boost for Hurkacz. Replicating that sort of performance will not be an easy task, especially against Berrettini, who has served incredibly well throughout the tournament. It's an intriguing and closely matched clash. Whomever comes out on top will have been able to handle the moment best and not let their game be dictated from the other side of the court.

Stubbs: Matteo has been my favorite on the bottom half of the draw since the beginning of the fortnight, so he has to play big on his serve and not allow Hurkacz to find his rhythm on the return games. Both players like coming into the net to finish points from time to time, so it will come down to whoever stays the course in looking for their opportunities to come forward and press their opponent under pressure. Both players will be extremely nervous, so whoever controls those nerves and plays with conviction will come out on top.

How do you explain the recent pipeline of up-and-coming Italian players on the tour, with Berrettini potentially breaking through to his first Slam final?

Cahill: The Italian women can take some credit for forging the way in the past 10 years. Flavia Pennetta, Francesca Schiavone, Sara Errani and Roberta Vinci have all won major titles or made major finals. It has created belief, desire and hunger in the next generation of men coming through the system. You can see it in all of the Italian men. They are fierce competitors and fight for every point.

Cambers: There's a lot to it. Each of the Italian men have all had their respective coaches for several years, while Italy has invested in Challenger events at home, embraced statistical analysis and while players have fed off each other. Berrettini is benefitting from it now.

Gilbert: Italy has done a great job at having a lot of challengers and futures events there, and it paid huge dividends for younger players.

Hamilton: Berrettini has taken inspiration from Italy's golden generation of Pennetta, Errani, Vinci and Schiavone. They allowed this batch of young Italian tennis players to dream and, as a result of their success, there was further investment in hosting their own events and an improvement in training facilities and the science behind the sport. Berrettini has also, of course, been inspired by Italy's journey to the Euro 2020 final.

Maine: Let's not forget the successful group of Italian women - including major winners Francesca Schiavone and Flavia Pennetta -- that perhaps started this trend and inspired a younger generation of girls and boys in their home country. Achieving what they did on the sport's biggest stages showed what was possible and brought attention and resources to the game.

Mcnamee: Success doesn't come out of nowhere, and as we have seen with Ons Jabeur over the tournament, having players perform on the biggest stage is key to creating a new pipeline of exceptional talents. Such is the nature of tennis. The successes of Flavia Pennetta and Francesca Schiavone would have brought widespread support to the sport in Italy and allowed everyone willing to pick up a racquet the chance to access better facilities and support.

Stubbs: Success breeds success. With the amazing amount of female players over the past decade, more young Italians started to really believe they could be a part of that culture, including young men. These guys are pushing each other, training together and capturing the spirit of the last decade of the women's dominance at the Grand Slam level. The training facilities in Italy are terrific as well and they are now reaping the benefits.

Time to make some predictions

Cahill: Djokovic and Berrettini will each win in four sets and advance to the final.

Cambers: Djokovic is the obvious favorite, but Shapovalov has the game to beat anyone when he puts it all together. If he does that, he can win. Hurkacz continues to surprise everyone, but Berrettini has so much confidence from his Queen's win and so much firepower, he will take some stopping.

Gilbert: Djoker in straight sets over Shapovalov, while I am leaning toward Berrettini in a tight four-set victory (although I hope I get surprised and it goes to five sets).

Hamilton: Djokovic will not underestimate Shapovalov and this will be by far his sternest test of the fortnight. But Djokovic will continue his charge for Grand Slam No. 20. Berrettini is the favorite, but don't be surprised if Hurkacz makes it through to the final. He's already shown immense courage, and his defensive game is superb.

Maine: Djokovic's experience and dominance on grass is simply too much for Shapovalov. Djokovic in four. While Hurkacz will make this competitive until the end, Berrettini's game is just too well suited for the grass to lose now. Berrettini in five.

Mcnamee: Shapovalov could pull out a surprise, but I just don't think this will be the year when Djokovic drops form. Berrettini and Hurkacz will play a tight match and will go to five sets. But, in the end, Berrettini has shown the better form and will win.

Stubbs: Berrettini and Djokovic will win and face off in the final.