Roger Federer’s bid for a record eighth Wimbledon title fell short Friday as Milos Raonic reached his first Grand Slam final against favorite Andy Murray.

Federer lost in the Wimbledon semifinals for the first time in his career, falling to Raonic 6-3, 6-7 (3), 4-6, 7-5, 6-3 in three hours and 24 minutes on Centre Court at the All England Club in London.

No. 2 Murray of Great Britain, the 2013 champion, beat 10th-seeded Tomas Berdych of Czech Republic 6-3, 6-3, 6-3 in less than two hours to reach the Wimbledon final on Sunday for the third time.

“Obviously to make a Wimbledon final is a good achievement and I’ve got one more to go on Sunday,” Murray told the BBC after the match.

“The older you get, you never know how many chances you’re going to get to play in Grand Slam final. I’m glad I managed to get through today. You learn from those matches for sure, those experiences in the past have helped me a lot, playing against some of the best players of all time.”

No. 3 Federer had a break point late in the fourth set that would have allowed him to serve for the match but Raonic held and later broke the Swiss in the final game of the set.

“This one clearly hurts because I felt I could have had it,” Federer said. “So close. It was really so, so close. It clearly hurts.”

The 25-year-old Raonic, seeded No. 6, became the first Canadian man in history to advance to the final of a Grand Slam tournament.

“An incredible comeback for me, really,” the 6-foot-5 Raonic said. “I was struggling there through the third and fourth sets. He was playing some really good tennis. And just on the little, little opening, I managed to turn it around. I’m by no means done what I want to be here to do.”

Raonic has had John McEnroe in his coaching corner since the Wimbledon warm-up tournament at Queen’s Club three weeks ago.

“What he told me today is: ‘Go out there, leave it all out there,’” Raonic said. “I showed a lot of emotion out there, always positive, and I think that’s what got me through. Mentally, I had one of my best matches in my history and my career.”

Federer had been 10-0 in Wimbledon semifinals, winning seven of his finals. Raonic avenged a Wimbledon semifinal loss to Federer in straight sets two years ago.

Federer, who turns 35 next month, was the oldest man to reach the Wimbledon semifinals since 39-year-old Ken Rosewall was runner-up in 1974.

Federer last won Wimbledon in 2012, the last of his record 17 Grand Slam championships.

“It’s a dream to win my eighth,” Federer said. “It’s not my only reason why I play tennis, just to be clear, otherwise I’ll go in a freeze box now and come out before Wimbledon next year.”

While serving at 2-1 down in the fifth set, Federer lost his footing on a deuce point and fell onto his stomach on the turf while trying to reach a passing shot. Federer went immediately to his chair and called for a trainer, who examined his left knee.

“I hope I didn’t hurt myself,” Federer said. “I don’t know at this point. I hope it’s not so bad. I walked it off. I was able to finish. But I don’t slip a lot. I don’t ever fall down. It was a different fall for me than I’ve ever had. I just hope I’m going to be fine. I believe I am, but I’ll know more tomorrow when I wake up.”

In Murray’s previous Wimbledon finals, he lost to Federer in 2012 and beat Novak Djokovic a year later.

On Sunday, Murray will be playing in his 11th major final. He won the 2012 U.S. Open but has lost the other eight times he has reached the championship match at a Grand Slam tournament.

The 29-year-old Murray beat Raonic 6-7 (5), 6-4, 6-3 in the final at Queen’s Club, winning in three sets. Murray has a 6-3 record against Raonic.

Six-time women’s champion Serena Williams stands one victory from her record-tying 22nd Grand Slam singles title when she faces Angelique Kerber on Saturday.

Kerber, who beat Williams at the Australian Open, will again attempt to deny the top-seeded American as the No. 4 German plays in her first Wimbledon final.