Canada’s Denis Shapovalov is through to his first Grand Slam semifinal after posting a 6-4, 3-6, 5-7, 6-1, 6-4 win over Russia’s Karen Khachanov on Wednesday at Wimbledon.

Shapovalov, seeded 10th at the All England Club, fired 17 aces in the match and won 86 per cent of first-serve points, which helped lessen the impact of his 10 double-faults.

Later Wednesday, Montreal’s Felix Auger-Aliassime missed a chance to join Shapovalov in the final four after a 6-3, 5-7, 7-5, 6-3 loss to No. 7 Matteo Berrettini of Italy.

Still, it was a breakout tournament for the 20-year-old Auger-Aliassime, who reached the quarterfinals of a Grand Slam for the first time in his career with a captivating five-set win over fourth seed Alexander Zverev of Germany in the fourth round.

The 22-year-old Shapovalov, from Richmond Hill, Ont., hit 59 winners to Khachanov’s 31 and converted five of his 19 break point chances in the match at No. 1 Court that took nearly 3 1/2 hours to complete.

The last break came at 4-all in the fifth set. Shapovalov converted his fourth break chance in that game when Khachanov sent a forehand long.

“I knew it was going to be a tough match against Karen,” Shapovalov said. “We played once before and it was really physical and difficult. I knew he was playing well going into (the match) and honestly I felt he was outplaying me for most of the match.

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“Everything was going his way, so in the fourth set I tried to step in a little bit and play more aggressively. I felt he got a little bit tired in the fourth set and I also stepped up.”

Shapovalov’s previous best performance at a Grand Slam was at least year’s U.S. Open, where he reached the quarterfinals.

Shapovalov faces top seed Novak Djokovic in the semifinals on Friday. Djokovic is looking for this third straight Wimbledon title and sixth overall.

“He’s the best player in the world but anything is possible,” Shapovalov said in his post-match interview.

“When you look at the scoreboard first thing on Friday it’s going to be 0-0. Nothing else matters.”

Djokovic has won all six of his previous meetings with Shapovalov, most recently posting a 7-5, 7-5 victory in the round robin the ATP Cup at Melbourne, Australia back in January.

Djokovic called Shapovalov one of the leaders of the next generation of tennis stars.

“Maybe he was not winning big matches over the last couple of years, (but) it seems like he’s maturing,” Djokovic said. “You would expect that from a player like him that has really an all-around game.

“Huge serve, lefty _ it’s always tricky to play someone who is left-handed on the quick surfaces _ he’s comfortable coming to the net. I think his movement has improved, and due to his movement he’s probably making less errors, which was part of the game that was troubling him.”

“You don’t get many opportunities against his service game, especially on grass,” he added.

This report by The Canadian Press was first published July 7, 2021.