Everything seemed to be going according to Roger Federer’s master plan—or Maestro plan—as he stepped up to serve at 5-6 in the fourth set against Milos Raonic in their semifinal at Wimbledon on Friday.

The seven-time champion had weathered an early Raonic power surge to lead two sets to one. He was playing an exceedingly clean, virtually error-free match; he hadn’t faced a break point since the early stages, and he had made deep inroads on Raonic’s serve in the fourth set. From the start, Federer’s strokes looked sharp, his serve was just as effective as his opponent’s and he had struck the right balance of aggression and thoughtfulness; his variety of spins and placements had kept Raonic off balance. Even Federer’s fist pumps and “Come on!” shouts were impeccably timed. While age wasn’t on his side in this matchup, the 34-year-old knew that history was: Before Friday, Federer was 10-0 in semifinals at Wimbledon.

Raonic, meanwhile, looked destined to end up on the wrong side of tennis history again. The 25-year-old Canadian, who has labored in the long shadows of Federer and the Big Four, had lost his other two Grand Slam semis to them. Now a third defeat looked likely.

As for Milos’ master plan, it appeared to have backfired. Advised by his super-coaches, John McEnroe and Carlos Moya, to bring the heat and leave the tank empty against Federer, the man known as the Missile had dutifully launched as many 140-m.p.h serves as he could. And it had worked for a set. But it also led to 11 double faults, two of them at crucial moments in the second and third sets. By the fourth, the normally icy Raonic had overheated. He was going for too much on his returns and ranting to himself after every mistimed shot. Federer must have liked what he was seeing across the net.

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At 5-6 in the fourth, Federer also liked his chances if he could push the set to a tiebreaker. A clutch server par excellence, he had won dozens of must-have tiebreakers on Centre Court over the past 15 years, including one two days earlier in his comeback quarterfinal win over Marin Cilic. When Federer went up 40-0 against Raonic, I turned my scoresheet over and, as I do for every tiebreaker, scrawled a line down the middle of the page and put the two players’ initials on either side of it at the top. There seemed to be no point in waiting.

“This was just what Federer was looking for,” said ESPN commentator Darren Cahill at that moment. "An easy service game."

When I looked up, the score was 40-15. Federer missed a serve long, and then another. Double fault, 40-30. Then, to the gasps of the crowd, Federer missed two more serves long. Deuce. He seemed to be rushing, and not brushing up on the ball fast enough. At the same time that Federer was losing control of his serve, Raonic was finding the timing on his return.

After smacking a forehand return winner in the deuce court, and a backhand return winner in the ad court, Raonic reached set point for the third time. Federer came up with a first serve, Raonic reflexed it back and Federer charged forward for what looked like an easy forehand winner. Instead, in the fortnight's most inexplicable moment, Federer spun his forehand short and directly at Raonic. As stunned as he must have been at his good fortune, Raonic didn’t blink: He drilled a backhand pass down the line for a winner. Instead of a tiebreaker, we were heading to a fifth set.

“He gave me a little opening at the end of the fourth,” Raonic said, “and I made the most of it.”

Instead of staying on the wrong side of history one more time, Raonic had crossed to the other side. In the fifth set, Raonic’s serve and return grew stronger, while Federer’s will, and body, faded. Federer was hollow-eyed to start the fifth; it’s a look of resignation that I’ve seen on him when facing Novak Djokovic and Rafael Nadal, but never against a player he usually handles, like Raonic; Federer’s fourth-set disaster must have been playing havoc with his psyche. By the middle of the fifth, his knee had also given way, and this famously graceful champion ended one rally in a place he has almost never been before on Centre Court: flat on his stomach, splayed out across the grass.

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“Opportunities were all around in the fourth set,” a somber Federer said later. “I think I pushed him on his service games to get the break, but I couldn’t get the job done.”

Asked about the double faults at the end of the fourth, Federer went from somber to flabbergasted.

“Something went wrong," he said. "I don’t know what. Can’t believe it. Unexplainable for me. I’m very sad about that, and angry. I would have liked to see a breaker because I was the better player for the set.”

Raonic might have been hard-pressed to disagree with that assessment, but he was ready for any dip in Federer’s play. For that, he credited the more demonstrative and overtly upbeat demeanor he’s carried through this tournament, and which has been encouraged by McEnroe and Moya. It also carried over to his game; Raonic really did drain the tank in this one, to the tune of 23 aces, 75 winners and 56 trips to the net.

“Today I sort of persevered,” he said. “...The attitude kept me in the match, and I think that’s what made the biggest difference. I was always positive and I was always looking for solutions.”

He also knew that this Federer, the 34-year-old Federer who has been through an injury-plagued season, was not quite the Federer we’ve seen in the past.

‘You’re playing who Roger is today,” Raonic said, “not who he’s been the past few years.”

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As he left, Federer took a long look back at Centre Court as he waved. Some interpreted it as a goodbye, but Federer said it was just a thank you for the “feeling” the crowd had given him during this fortnight. As always, even without holding up the trophy, he had given that feeling right back to them. Despite his disappointment, Federer said he would hang on to the memory of his epic win over Cilic.

Once we liked to compare Federer to Tiger Woods; today, the golfer who came to mind while I watched Federer leave was Jack Nicklaus. That’s a promotion, of course, but like Nicklaus—who won 18 majors and finished second 19 times—Federer has suffered his share of tough defeats late at the Slams in recent years. The same player who won his first six Slam finals has lost four of his last five. When a champion plays for long enough, the epic losses will pile up next to the epic victories. Whether he’s winning or losing, Federer has brought as much entertainment, drama, joy, and pain to the crowds in Centre Court as any player in that arena's 96-year history.

This year, rather than watching Federer’s 11th Wimbledon final, we’ll see Raonic’s first. In 2011, British tennis writer Richard Evans predicted that Raonic would win this tournament in four years. He may have taken an extra year to get to the mountaintop, but Raonic was ready when his moment came.

Yet as I looked back through my match notes on Friday, I came across the line that I had scrawled, with the initials "RF" and "MR" at the top, in anticipation of a fourth-set tiebreaker. What would have happened if they had played it? Happily for Raonic, and unhappily for Federer, the rest of the page is empty.