Novak Djokovic has been the heavy favorite to win it all at Wimbledon. And entering the men's semifinals (Friday, ESPN, 8 a.m. on the ESPN app), he is on the cusp of his 20th career Grand Slam singles title.
Could first-time Slam semifinalist Denis Shapovalov be in trouble? And what should we expect in the second matchup between two more Slam semi-final first-timers Matteo Berrettini and Hubert Herkaz?
Our tennis gurus tell you what to look for and make your predictions.
ESPN TV analyst Darren Cahill: Dennis can be a disruptor with his ball-striking prowess. The way he played the last two sets of his quarterfinal match against Karen Khachanov, he has a good blueprint: Hit with a good margin until you find the right ball to attack, and then launch. Breaking the court with his left forehand will open up opportunities, but it is the focus of his service game that will be important. Novak will continue to put pressure on his return games by limiting the free points he gets on Dennis' serve. He needs to keep his first serve percentage around 65 and a forehand-body serve to Novak will be a good game. He'll need Novak to spend an average day, because if Novak is close to his best, he's not losing to anyone.
ESPN Tennis Contributor Simon Cambers: Shapovalov has to serve well. His Achilles heel is a double defect. If he serves well and overcomes double faults, he will give himself a real chance.
ESPN TV Analyst Brad Gilbert: Shapstick is going to have a good day on his serve and take a lot of chances with his forehand. Still, even if Canadians are hot, beating the Joker on the grass is the big question.
ESPN Writer Tom Hamilton: Shapovalov has an amazing backhand - he winds it up and then blasts the ball through. Andy Murray found it difficult to deal with in his third round match. Shapovalov also needs to make sure that he manages his service well. Against Karen Khachanov, he won only 50% of the points on his second serve and had 10 double faults.
ESPN writer D'Arcy Maine: Even if Shapovalov is playing his best tennis, it will still be a huge challenge. This is the reason Djokovic has won all his last six matches. Still, as Shapovalov said several times on Wednesday, "anything is possible," and he is right. His lefty serve could do some damage, as against Khachanov, and even Djokovic admitted how difficult it was to get opportunities during Shapovalov's serve games. He has to take advantage of every opportunity out there and stay mentally strong. After winning the first set on Wednesday, Shapovalov lost the next two sets and then fought to win. He has to have the 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 his one-on-one record and Djokovic's general form at the moment shows the Serb has the upper hand . This will be especially important for his service game, which he has used on points but has struggled with double faults.
ESPN TV analyst Rene 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 Novak from that side on his return. He has such a great attitude that, I believe, he needs to use it and try to get the crowd on his side and try to get under Novak's skin. Nowak is kind of off 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.
Cahill: A win at Wimbledon doesn't change anything for Novak, but if he wins Wimbledon and the US Open this year don't hesitate to ask me that question again. He may be the greatest man of this generation anyway, but a Grand Slam would basically make it in stone.
Cambers: It's too early to say. Djokovic will be in pole position given his age and he is still No. 1, but things may change, and total number of slams may not be the only relevant criterion.
Gilbert: For me, now there is zero point in discussing the goat. The Joker will have a few more chances to win more Slams in the next few years, so we won't have an answer then.
Hamilton: It all depends on your own subjective criteria. If it is at the Grand Slams alone, Djokovic will emerge from this golden period in the sport with the most singles titles. If it's aesthetics, you might like Roger Federer or Rafael Nadal. Either way, this debate will continue even after the three great players retire. For most, it will be Federer.
Main: Even if Djokovic doesn't get to No. 20 this weekend, he will undoubtedly be from the US Open, and that's why he's already topped the goat talk for me. Federer and Nadal do not look alike these days, while Djokovic is still at his peak. I don't think there's any question that Djokovic will take sole possession of the record anytime soon, and I wouldn't be surprised if he captures Serena Williams' Open Era record of 23.
Mcnamee: If you're basing the debate solely on Slam wins, a Wimbledon title would certainly put him ahead of the others. However, after seeing how the crowd has loved Federer over the past two weeks and the level he has achieved after so many serious injuries, it is too early to judge Djokovic's legacy.
Stubbs: There's no doubt in my mind that Novak is going to win the calendar Grand Slam this year, as well as possibly add an Olympic gold medal to what Steffi Graf did. He's so impressive right now, it's going to take the match of someone's life to beat him, especially over 5 sets; This is possible in three sets at the Olympics, but is harder to do at the Grand Slam level. If he wins all four Slams in one year, it will eventually put the veil on Goat's argument. He's been so dominant over Roger and Rafa over the past decade, and once he's passed them on the slam count, there's no more reasoning.
What are the keys to Berrettini and Herkaz in their struggle?
Cahill: Harkaz has done a remarkable job in his last two matches against two different opponents. He has shown the ability to change his game plan. Against Berrettini, it will be different again, with enormous power coming from the serve and forehand. He'll zone in Berrettini's backhand, but sometimes you have to play with strength to find the weak side, and that's dangerous. Ultimately, Herkaz would like to encourage Berrettini to play the backhand passing shot, especially at the big points. A game of cat and mouse is a must have 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 all about the serve. If Berrettini makes a good serve, he can snatch the match out of Harkaj's hand. Hurkaz made a good comeback against Federer. He'll have to do the same thing again.
Gilbert: It's a very open matchup between Hurk Locker and Berrettini. It comes down to who handles the occasion and the occasion, as both have great serve and both will want to dictate from the center of the court.
HAMILTON: Harkaz came back well against Federer but needs to convert more break points (just five out of 15 against the Swiss great). It will be a fight of offense against defense. Berrettini serves big (he has 79 aces at Wimbledon) and is famous for his powerful forehand. But, as Harkaz proved at Wimbledon, he can handle anything thrown at him.
Main: Berrettini's serve has been a great weapon and he needs to continue to use it and his strong forehand. After winning the title at Queens, she is on a 10-match winning streak and her current confidence and pace could prove to be unstoppable.
Harkaz won the biggest match of his life against Federer, never letting himself be intimidated by the moment. He needs to bring the same level of calm to the semi-finals and not get carried away with what is at stake now. Both players know this is an incredible opportunity, so it may come down to who can handle their nerves and pressure better.
McNamee: Beating Federer in front of a crowd of spectators would have been a big boost for Harkaz. It will be no easy task to replicate that kind of performance, especially against Berrettini, who has done incredibly well throughout the tournament. It is an intriguing and closely matched conflict. Whoever comes out on top will be able to handle the moment the best and not let their game be decided by the other side of the court.
Stubbs: Matteo has been my favorite at the bottom of the draw since the start of the fortnight, so he has to play big on his serve and not allow Herquez to find his rhythm in the return game. Both players like to get into the net from time to time to score points, so it will be down to who is looking for opportunities to come forward and put their opponent under pressure. Both players will be extremely nervous, so whoever controls those nerves and plays with conviction will come out on top.
Cahill: Italian women can take credit for leading the way in the last 10 years. Flavia Pennetta, Francesca Schiavone, Sara Irani and Roberta Vinci have all won major titles or made it to major finals. It has instilled faith, desire and hunger in the next generation of people to come through the system. You can see it in all Italian men. They are fierce competitors and fight for every point.
Cambers: There's a lot to it. The Italian men have each had their own coach over the years, while Italy has invested in Challenger events at home, adopting statistical analysis and players feeding each other. Berrettini is now reaping the benefits.
Gilbert: Italy has done a great job in a lot of Challengers and Futures events, and it has paid huge dividends for the young players.
Hamilton: Berrettini draws inspiration from Italy's golden generation Pennetta, Irani, Vinci and Schiavone. They allowed this batch of young Italian tennis players to dream up and, as a result of their success, further investments were made in hosting their own events and improving training facilities and the science behind the game. Berrettini is also, of course, inspired by Italy's visit to the Euro 2020 final.
Maine: Let's not forget the successful group of Italian women—including major winners Francesca Schiavone and Flavia Pennetta—who probably started the trend and inspired a younger generation of girls and boys in their country. Achieving what he did in the biggest stages of the game showed what was possible and brought attention and resources to the game.
Mcnamee: Success doesn't come out of nowhere, and as we've seen with Ones Jabur in tournaments, getting players to perform on the biggest stage is the key to building a new pipeline of exceptional talent. Such is the nature of tennis. The successes of Flavia Pennetta and Francesca Schiavone would have given wider support to the sport in Italy and gave everyone a chance to use better facilities and support to take the racquet.
Stubbs: Success breeds success. With the amazing number of female players in the past decade, more young Italians are beginning to truly believe that they can be part of that culture, which includes young men as well. These guys are pushing each other, training together and capturing the spirit of the last decade of women's dominance at the Grand Slam level. The training facilities in Italy are also great and they are taking advantage of it now.
Cahill: Djokovic and Berrettini will win four sets each and advance to the final.
Cambers: Djokovic is clearly the favorite, but Shapovalov has the game that can beat anyone when he puts it all together. If he does, he can win. Harkaz continues to surprise everyone, but Berrettini is so confident of his queen's victory and so much firepower, he'll hold off on something.
Gilbert: Joker in straight sets over Shapovalov, while I'm leaning toward Berettini in a hard four-set win (though I expect to be surprised and it goes to five sets).
HAMILTON: Djokovic won't underestimate Shapovalov and this will be his toughest test of the fortnight so far. But Djokovic will continue his charge for Grand Slam No. 20. Berrettini are the favourites, but don't be surprised if Herkaz makes it to the finals. He has already shown immense courage and his defensive game is superb.
Main: Djokovic's experience and dominance on the grass are too much for Shapovalov. Djokovic in four while Herkaz will make it competitive until the end, Berrettini's game is very fit for grass to lose right now. Berettini 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.