The first thing I thought of when Sam Querrey beat Novak Djokovic in the third round at Wimbledon was that Milos Raonic’s opportunity had arrived. Not Roger Federer’s opportunity, although removing the nimble Serbian obstacle from the loaded top half of the draw could potentially smooth the Swiss’ path toward a record 18th Grand Slam singles title. But it was Raonic, runner-up at the grass-court tune-up at Queen’s Club and still waiting for that proverbial “breakthrough” at a major, who was my favorite to reach the final.

There were no excuses left for the towering Canadian, who has employed the services of Carlos Moya and John McEnroe (combined, they’ve won a career Slam) in order to help him raise a Grand Slam trophy for the first time. The 25-year-old had reached two prior major semifinals, pocketed eight tour titles and has generally been considered the most likely to succeed outside of the Big Four for some time. But he had to, as Nike famously puts it, just do it.

He did do it, though for much of this match, it seemed that Raonic would again fail to deliver at the most critical time at the most important tournaments against the most accomplished players. After taking the first set, 6-3, Raonic was bested in a tiebreaker and offered Federer two break chances in the third set, one of which was converted. Federer was the sharper player, and when he continued to make inroads on Raonic’s serve in the fourth set—he earned three break points, but couldn’t win any of them—it seemed that experience would once again prevail, as it has for so often on the ATP tour.

Then, one point away from a fourth-set tiebreaker, everything changed. Leading 40-0, Federer dropped his next service point and then inexplicably double-faulted twice to hand Raonic an unlikely lifeline. Emboldened, Raonic made Federer pay for the rare but massive sequence of mistakes, winning the fourth set, 7-5, before running away with the decider. To add injury to insult, Federer took a tumble on the Centre Court turf while running for a ball. The trainer came out to look at his ankle, but the real damage was already done.

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Although I considered Raonic a slight favorite heading into this match, that doesn’t mean the loss hurts Federer any less. You could see it in his face, his eyes and his body as he glumly walked off Centre Court, giving his supporting fans acknowledgment at only the very last instance. When you consider the stakes, the opportunity afforded by Djokovic’s exit and Federer’s age, I believe this will go down as one of his toughest defeats.

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This isn’t Federer’s first dalliance with heartbreak at Wimbledon; far from it. And it’s not his first late-round match at a major he—possibly?—should have found a way to win. In the 2009 U.S. Open final, Federer was in control against young Juan Martin del Potro, another booming hitter who’d yet to prove he could win it all. It was another series of critical mistakes that doomed Federer in that match-up, which reminded me of today’s contest in a lot of ways. Like Raonic, del Potro ran away with the fifth set.

You have to give full credit to Raonic for taking the match when so many other players—Marin Cilic, anyone?—left it in Federer’s hands. But you can’t escape the feeling that this is a missed opportunity Federer that will rue for a long time.