Milos Raonic defeated Australian qualifier Nick Kyrgios 6-7, 6-2, 6-4, 7-6 (4) to join fellow Canadian Eugenie Bouchard in the semifinals at Wimbledon.
It’s the first Grand Slam semifinal appearance for Raonic, who finished Kyrgios off with an ace after the Australian had saved three match points in the fourth-set tiebreaker.
Raonic, from Thornhill, Ont., will face Roger Federer in the semifinals. Federer advanced with a 3-6, 7-6 (5), 6-4, 6-4 win against fellow Swiss Stan Wawrinka.
The 144th-ranked Kyrgios, who upset Rafael Nadal in the fourth round on Tuesday, was attempting to become the first wild card to make the semifinals at a Grand Slam since Goran Ivanisevic at Wimbledon in 2001.
The last Canadian man to reach the Wimbledon semis was Robert Powell in 1908.
Earlier, Bouchard, form Westmound, Que., advanced to her third straight Grand Slam semifinal with a 6-3, 6-4 win over Angelique Kerber.
The 13th-seeded Bouchard also made the semfinals at the French Open last month and the Australian Open earlier this year.
She will face French Open finalist and third-seed Simona Halep after the Romanian crushed 2013 Wimbledon finalist Sabine Lisicki 6-4, 6-0 on Wednesday.
The win is expected to put the 20-year-old Bouchard into the WTA’s top-10 for the first time in her career.
“I’m excited to be in the semis. But, of course, I’m never satisfied, so I definitely want to go a step further, or as far as I can,” Bouchard said.
“I’m looking forward to try to play a little bit like I played today. I thought I was pretty solid out there and playing the right way on the grass. So that’s going to be a key.”
In other men’s quarter-final action, defending champion Andy Murray was defeated in straight sets by Bulgaria’s Grigor Dimitrov. Dimitrov next faces top seed Novak Djokovic, who reached the Wimbledon semifinals for the fifth consecutive year by coming back to beat 26th-seeded Marin Cilic of Croatia 6-1, 3-6, 6-7 (4), 6-2, 6-2.
Bouchard says she’s ready to get beyond the final four.
“I’m excited to be in the semifinals against (her) but I want to go further for sure,” said Bouchard.
Canada’s Fed Cup captain Sylvain Bruneau said he’s not putting a limit on how far Bouchard can go.
“Can she be No. 1 one day? I wouldn’t dare to put any limits on Eugenie,” he said. “With three semifinals at 20 years old and the type of tennis she plays, I don’t think there is a limit. I think she can aim for big things in tennis. No. 1 in the world is something that is very possible.”
Bouchard struggled to close out her win over Kerber, whom she beat a month ago in Paris.
She finally advanced after 72 minutes on her first match point, which she set up with a down-the-line winner followed a point later by a Kerber backhand error.
“It was a tough battle, I’ve played her before and I knew what to expect,” said Bouchard. “I had to just keep fighting and I pulled it out at the end.”
Bouchard saved two break points in the final game and ended with three breaks of serve from 13 chances. She had 29 winners and 20 unforced errors.
“In the last game, I was just trying to stay in the moment,” said Bouchard, who improved her Wimbledon record to 7-1. “I was not thinking ahead. That’s something I’ve been working on.”
“I had a few bad errors in that game but I also hit some aggressive shots, that’s just my game,” she added.
Bouchard has lost her only previous meeting against Halep, on hardcourt at Indian Wells last March.
“She’s a good player and I’m ready for another tough match,” Bouchard said.
“It’s not every day you can walk out on Centre Court and play the semis of a slam. That’s the most important thing for me, is to really enjoy it. I’m going to try, give it my best, leave everything on the court, and we’ll see what happens.”
Halep, meanwhile, took command of her match by attacking Lisicki’s weak second serve. The German won only eight of 26 points on her second serve. She also had 20 unforced errors, compared to 11 by Halep.
“She had 4-1 and then I came very well back,” Halep said. “I played my best today and I was enjoying every moment because it was incredible on Centre Court.”
Murray’s reign as Wimbledon champion ended with a loss to Dimitrov, who is making his breakthrough after years of being touted as the game’s next top player.
Dimitrov completely outplayed Murray on Centre Court, winning 6-1, 7-6 (4), 6-2 to reach his first Grand Slam semifinal.
The 11th-seeded Dimitrov broke Murray five times, including in the final game, to become the first Bulgarian man to advance to the final four of a major. It was his first victory over a top 10 player at a Grand Slam.
Murray last year became the first British man to win Wimbledon in 77 years. He came into the quarter-finals riding a 17-match winning streak at the All England Club and had not dropped a set this tournament.
“He was the better player start to finish,” Murray said.
Murray fell flat while Dimitrov lived up to his promise on the biggest stage in the game.
“To win any tournament back-to-back, let alone back-to-back on a surface like this which sometimes rests on a few points in a set, it’s not always going to go your way,” Murray said. “Grass is a tough surface to do it on, but I didn’t feel like that had any bearing on my outcome.”
Dimitrov’s win marked a huge step forward for a player nicknamed “Baby Fed” because of a style of play — especially the one-handed backhand — resembling that of Federer. The 23-year-old Dimitrov is also well known for being the boyfriend of Maria Sharapova.
He took the initiative right from the start against Murray and never looked back.
“As soon as we started warming up I sensed that his game was not at the highest level but at the same time I was feeling pretty confident,” Dimitrov said. “The first set really helped me get into a good rhythm and then I was just holding my ground throughout the whole match.”
The statistics told the story: Dimitrov served 10 aces and had 32 winners and 18 unforced errors. Murray served as many double faults (5) as aces and had more unforced errors (37) than winners (24).
“Today was a bad day,” Murray said. “I made many mistakes. I think I had one backhand winner the entire match which isn’t normally what I do, especially on this surface. So it was a tough day all around.”
Among those in the Royal Box were Prince William, second in line to the British throne, and his wife Kate.
In men’s doubles, Vancouver’s Vasek Pospisil and American Jack Sock reached the quarter-finals with a 7-6 (3), 7-6 (3), 6-4 win over Croatian Mate Pavic and Andre Sa of Brazil.
— With files from The Associated Press