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WATCH: Djokovic in press following his quarterfinal victory

Novak Djokovic vs. Denis Shapovalov

Watching Shapovalov finish up his quarterfinal win over Karen Khachanov on a high note on Wednesday, I wondered if he was the type of player who could put a serious scare into Djokovic. At his best, as he showed down the stretch against Khachanov, Shapo can fire off unplayable forehands and backhands left and right, and his lefty serve is a formidable bailout weapon on grass. To beat Djokovic, you’re probably going to have to take the racquet out of his hands, and Shapovalov can do that.

Just when I was starting think an upset was something less than impossible, I looked up and saw a sobering graphic: Djokovic is 6-0 against Shapovalov. He has lost a stray set to him here and there, and they played a very good 7-5, 7-5 match at the ATP Cup this January; but Shapo hasn’t found a way to sustain his peak level long enough to get a win. And that will be the issue again when they meet in the semifinals on Friday. Shapovalov may come out guns blazing, get the crowd behind him, and win a set. But even if all of that does happen, Djokovic will know that he still has two more sets to go. Winner: Djokovic

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Djokovic is the first man to reach 10 major semifinals on three different surfaces; the other three combined have one prior major semifinal appearance in total. (Getty/AP Images)

Djokovic is the first man to reach 10 major semifinals on three different surfaces; the other three combined have one prior major semifinal appearance in total. (Getty/AP Images)

Matteo Berrettini vs. Hubert Hurkacz

This is not the semifinal that most fans had on their Wimbledon bingo cards, and it’s not exactly a broadcaster’s dream, especially when Roger Federer was one win away from being in it. But Hurkacz and Berrettini have both been building to a big Grand Slam result in 2021. The Pole won a Masters 1000 title in Miami, and the Italian has now won 10 straight matches on grass. Berrettini is ranked nine spots ahead of Hurkacz (No. 9 to No. 18), but Hurkacz won their only previous match, in straight sets in Miami two years ago. There are reasons to like both of these guys’ chances. Berrettini has been muscling people off the court convincingly, and has dropped just two sets so far. But Hurkacz has a win over No. 2 seed Daniil Medvedev, and he just handed Federer his first bagel set at Wimbledon. We’ll see who serves and returns better, but once the rallies start, I like Hurkacz’s forehand, which he can flick in any direction he chooses, and his ability to create openings to move forward. Winner: Hurkacz