Three of the men’s semi-finalists on Friday have one main problem. The fourth man. Novak Djokovic. In the past 10 years at Wimbledon, three men have beaten him in completed matches: Roger Federer in the semis in 2012, Andy Murray in the final in 2013 and Sam Querrey in the third round in 2016. Djokovic also lost to Tomas Berdych in 2017, but on that occasion, he retired hurt with an elbow injury, so the size of the task facing Denis Shapovalov, and by extension the other two semi-finalists, Matteo Berrettini and Hubert Hurkacz, is clear. Djokovic has looked in imperious form throughout his first five matches, dropping one set, the first he played against the British teenager Jack Draper. With the exception of one tiebreak against Denis Kudla in the third round, no one else has taken more than four games in a set. It is five years since Shapovalov was winning the junior singles title here, the same year Murray won his second Wimbledon title. The Canadian’s progression toward the top of the game has been relatively swift and he is guaranteed to be ranked inside the top 10 after this week. For all his talent, though, he has won one title, in Stockholm in 2019, and this will be his first time in a grand slam semi-final. By contrast, the five-time champion Djokovic is in the last four at Wimbledon for the 10th time and will be playing his 41st grand slam semi-final. Victory for the Serb come Sunday would put him level with Federer and Rafael Nadal on 20 grand slams, so the incentive for him is obvious. Shapovalov, though, has the kind of game that could prove awkward if Djokovic is not completely on song. Left-handed, he has a big serve, aggressive groundstrokes, excellent movement and a willingness to come forward. Like many young players with a lot of weapons at their disposal, it has often been hard for him to make the right choice, shot selection letting him down at times. But as he showed at last year’s US Open, when he reached the quarter-finals, and over his five matches here, including a demolition of Murray in the third round, he has been maturing fast. Watching him rise through the ranks it always seemed likely that big things would happen once he put it all together. The maturity he showed in his win over Karen Khachanov in the last round, coming from two sets to one down, is also a good sign. “From juniors, from a young age, I never was a player that would sit back and wait for my opponent’s mistakes,” he said. “I always wanted to be the one dictating. I was always coming to the net from 10, 12 years old. Getting lobbed back there, losing points. “My mom always told me later on you’re going to grow and this is going to be an advantage to you. It’s something that is yours, you have to keep and maintain it for the future.” If he is going to have a chance, though, he will need to serve well against perhaps the best returner the game has seen. Though his serve is a big weapon, it can also be his weakness; Shapovalov has served more double faults than anyone in the tournament, with 37 in five matches. He has also lost his previous two matches with Djokovic, who has lost one semi-final in a slam since 2014. But the 34-year-old world No 1 knows the threat he possesses. “I’ve seen him play against Murray,” Djokovic said. “It’s impressive the way he’s been playing. I’m sure that’s going to be the biggest test I will have so far, which is also expected. It’s semi-finals.” Berrettini and Hurkacz will be appearing in their first Wimbledon semi-final. The Italian, who won the title at Queen’s Club last month, has the greater experience having reached the last four at the US Open two years ago; the Pole has the belief having beaten the eight-time champion Federer in the quarters here. With Djokovic still going strong, the title remains a long way off for them but you just never know for sure what is going to happen. As Jimmy Connors liked to say: “That’s why we put up the net.”