Denis Shapovalov thanked the crowd for helping him into a semi-final against Novak Djokovic after five nip-and-tuck sets against on No 1 Court on Wednesday, but it was as much as case of the No 10 seed needing to persuade himself as anything else. Shapovalov gave himself the fiercest talking-to of several after falling 2-1 behind, having handed Karen Khachanov a crucial break point in the third set with a double fault, and it seemed to do the trick as the persistence and accuracy of the Canadian’s shot-making, and his one-handed backhand in particular, finally proved too much for his Russian opponent. The towering figure of Khachanov, five inches taller than his opponent at 6ft 6in, gave this quarter-final – the first for both players – a David and Goliath feel, but Shapovalov had more to his game than service winners and bludgeoned forehands, matching his opponent shot for shot for much of the three-and-a-half hours. It was only in the final set, as Khachanov visibly tired and he was increasingly drawn into extended rallies in his services games, that Shapovalov was able to plot a path to the semi-finals. A fifth set seemed unlikely after a first which turned on Shapovalov’s third service game. The Canadian dug himself into the first of what proved to be several holes over the course of the match, opening up with two double faults and an invitingly short second serve to go 0-40 down. Having hauled it back to deuce, Shapovalov then slipped into further trouble with another double fault, before a service winner and a brilliant forehand swung the momentum back in his direction. Having spurned four break points there, Khachonov then offered Shapovalov his first at 4-4, when a wonderful backhand return found the line to set up a volleyed winner at the net. Shapovalov duly served it out to love, but by the time he won his serve again, he was already 4-1 down in the second after a pair of sloppy service games, the second of which he surrendered from 40-0. His frustration was palpable as the set slipped away, and when the gremlins returned at the end of the third set too, the No 25 seed was suddenly the favourite to progress. After a full and frank exchange of views with himself, though, Shapovalov was a different beast in the fourth, reeling it off 6-1, and while the fifth was closer, Shapovalov’s serve was largely untroubled while Khachanov’s service games were increasingly more of a struggle. The ninth game was the clincher, as Khachanov opened up with a beautiful forehand into the corner and then a service winner before dropping a double fault to let his opponent back into the game. Sensing blood, Shapovalov was soon at break point and while Khachanov saved that and then saw Shapovalov put a forehand long when it should have been a game winner, two errors at the fourth deuce – one wide, one long - handed his opponent the vital break. “Honestly, I felt that he was outplaying me for most of the match,” Shapovalov said. “Obviously, I had some chances, but he was playing really, really well in those. Kind of everything was going his way. “In the fourth set, I tried to actually step in a little bit and play a little bit more aggressively. I felt that he fell a little bit physically, got a little bit tired there in the fourth set. I also stepped up [and] I felt really good going into the fifth set.” Shapovalov has lost all six of his previous matches against Djokovic, although the semi-final on Friday will be their first meeting on grass. “It’s nothing I’m really thinking about too much,” he said. “When you walk out on that match, it’s 0-0. That’s it. It’s a tennis match at the end of the day. Experience, this, that, it comes down to that moment and who’s playing the best.” Matteo Berrettini, the seventh seed, made shorter work of the second quarter on Court No 1, though it took four sets for his power on serve and forehand to overwhelm Felix Auger-Aliassime, who was bidding to become the second Canadian into the semis, 6-3, 5-7, 7-5, 6-3. His big first serve was generally there when Berrettini needed it and the Queen’s Club winner will go into Friday’s tomorrow’s semi-final against Hubert Hurkacz as the clear favourite to extend his run of 10 straight victories on grass.