Canada's Milos Raonic dropped a 6-4, 6-4, 6-4 decision to Switzerland's Roger Federer in men's singles semifinal play Friday at Wimbledon.
It was Raonic's first appearance in a Grand Slam semifinal. Federer will next play Serbia's Novak Djokovic, a four-set winner over Bulgaria's Grigor Dimitrov in the early semifinal.
Raonic's loss leaves Eugenie Bouchard of Westmount, Que., as the last remaining Canadian in singles play. On Saturday, Bouchard will try to become the first Canadian to win a Grand Slam singles title. She will play Petra Kvitova of the Czech Republic in the women's final.
Raonic, from Thornhill, Ont., has lost all five career matchups against Federer, who will go for his eighth career singles title at the All England Club. It will be the Swiss star's 25th appearance in a Grand Slam final.
Federer, who owns 17 Slam titles, is back in a major final for the first time since winning Wimbledon in 2012. Earlier, the top-seeded Djokovic ran off six of the final seven points in the tiebreaker to beat Dimitrov 6-4, 3-6, 7-6 (2), 7-6 (7) to advance to his third Wimbledon final in four years.
It's Djokovic's 14th Grand Slam final — and 10th in his last 13 majors.
Raonic appeared a little nervous at the start of the match Friday, with Federer breaking his serve in the opening game. Federer picked up one break in each of the following sets and never appeared threatened.
Before this tournament, no Canadian had ever reached a men's or women's Grand Slam singles final, according to Tennis Canada. The last Canadian to reach a singles semifinal at a major was Robert Powell at Wimbledon in 1908, the organization said.
Montreal native Greg Rusedski reached the U.S. Open final in 1997 but he was representing Great Britain at that time.
Raonic had not been past the second round in each of his three previous appearances at Wimbledon. He will rise three positions to a career-best ranking of No. 6 when the new ATP rankings are released Monday.
Djokovic, the 2011 champion and runner-up last year, overcame the loss of five straight games in the second set, seized control with a more aggressive game and took advantage of eight double-faults by Dimitrov — including three in a row in the third game of the fourth set and one in the final tiebreaker.
Djokovic is going for his seventh Grand Slam title. He lost in his last two major finals, falling to Rafael Nadal at the French Open last month and at the 2013 U.S. Open.
"All these matches, (I) could have won, so I'm looking forward," Djokovic said. " It's a big challenge, it's a big match. Whoever I play in the finals, I have to be on top of my game. This is Wimbledon final, and it's the biggest event we have in (our) sport."
The 11th-seeded Dimitrov, with his girlfriend Maria Sharapova watching from his guest box on Centre Court, came in with a 10-match winning streak and had been seeking to become the first Bulgarian to advance to a major final. Nicknamed "Baby Fed" for a style of play resembling Federer's and long billed as the game's next big thing, he pushed Djokovic to the limit but came up short when he could have forced a fifth set.
"His first semifinal, but he was fighting," Djokovic said. "It was a tough match. Fourth set could have gone either way. ... But overall, I'm just really glad to reach another Wimbledon final."
The match seemed to be headed for a fifth set when Dimitrov went up 6-3 in the tiebreaker, giving him three set points. But Djokovic held firm and erased all three. Dimitrov then served his eighth double fault to go down 7-6, handing Djokovic a match point.
Dimitrov saved that one with a forehand pass to make it 7-7. Djokovic hit a forehand winner on the next point as Dimitrov slipped to the turf — one his many tumbles. Djokovic then closed out the match with a forehand passing shot that clipped the top of the net.
Dimitrov showed flashes of his talent, hitting more winners than Djokovic (48-45) but had more unforced errors (33-26). Each player broke serve three times.
The match was played in tough conditions, with a swirling wind and slippery grass at the back of the court causing problems for both players. Dimitrov struggled particularly with his footing. On one point in the third set, both players ended up face forward on the grass after an exchange near the net.
Djokovic looked in command after winning 20 of 24 points on his serve to take the first set and going up a break at 3-1 in the second. He had a break point with a chance to go up 4-1, but Dimitrov saved that with an ace and went on to take five games in a row and the set.
The momentum seemed to be with the Bulgarian, as he kept Djokovic at bay with low, slice backhands and forehand winners.
But the match turned back in Djokovic's favour on a key point at 3-3 in the third set. On a break point, Dimitrov attacked Djokovic's second serve with a deep forehand return. Djokovic hit a lucky backhand that dropped into the court for a winner.
Dimitrov played a poor third-set tiebreaker and looked deflated after serving a double-fault into the net to fall behind 5-2.
At 1-1 in the fourth set, Dimitrov did something few players do — he served three straight double-faults to go down 0-40. He hit a forehand long on the next to go down a break. Yet Dimitrov showed resolve, breaking right back in the next game with a cross-court forehand winner.