What's the one that got away from Roger Federer?

The One That Got Away. It’s one of the oldest themes in the book, and we’re not talking about The Angler’s Digest. Everyone seems to have experienced an unexpected, perhaps even undeserved loss that still inspires regret. It could be a job, a romantic partner, an investment opportunity, a ... well, a fish. Or a critical tennis match.

Over the coming days, Tennis.com will revisit the most surprising, significant defeats suffered by three iconic tennis stars: Rafael Nadal, Roger Federer and Novak Djokovic.

2019 Wimbledon Final

Novak Djokovic d. Roger Federer 7-6(5), 1-6, 7-6(4), 4-6, 13-12(3), in 4:57.

• Age: Federer, 37, Djokovic 32
• Major Titles: Federer 20, Djokovic 15
• Major Final Meetings: Djokovic led, 3-1
• All Meetings: Djokovic led, 25-22

It was probably, mentally, the most demanding match I was ever part of. Novak Djokovic

The Wimbledon final of 2019, that painful one-that-got-away from Roger Federer, was historic in multiple ways. It was the first Wimbledon tournament to embrace a final-set tiebreak. Despite that, it was also the longest of all Wimbledon finals—just three minutes shy of five hours. But neither the stats nor the record book will tell the extent to which this match was more noteworthy as a history-shaping event.

This was the point at which Federer stumbled and surrendered what once seemed like a safe lead in the intense, if undeclared, race to become the men’s all-time Grand Slam singles champion. It was the final step in the evolution of Novak Djokovic into the most successful player in the history of the game.

None of this was foreseeable, because “Fedal” (Federer/Nadal) still dominated the public imagination. Their semifinal was the most hotly anticipated match of the event to that point. It went to Federer (surely, many thought, a sign of things to come) the the eight-time champion who was celebrated, for reasons extending well beyond his record, as a kind of avatar of the tournament.

With 20 major titles, Federer still led Nadal by two titles. Djokovic was far behind with 15, and had recently endured two turbulent years (2016-17)  marked by self-doubt, injury and existential restlessness. At one point, he even fell out of the Top 20 before finding his best game again at Wimbledon in 2018. That was his fourth Wimledon title, and 13th major.

“Every time I step on the court, I reflect on what has happened the previous year,” Djokovic said in 2019, characterizing his rebound in 2018 as "huge, just huge."

"After that, I started to play my best tennis," he said. "That got me [back] to No. 1. Wimbledon has a special place in my heart for many different reasons.”

All those reasons would come in handy as emotional fuel for Djokovic because, as he said afterward: “It was probably, mentally, the most demanding  match I was ever part of. The most physically demanding match was against Nadal in the finals of Australia [2012]. But mentally this was a different level, because of ... everything.”

One of the main “everythings” was the near-universal support Federer would enjoy.  Djokovic prepared by running the various challenges posed by partisan fans through his mind before the encounter. Thus, when he heard the chant of, “Let’s go, Roger!” during the match he mentally joined in - but transformed the name to his own.

Djokovic had no illusions about being able to take the fans out of the match. Centre Court was as much Federer's house as Roland Garros belonged to Nadal, and Djokovic was still the intruder in their bromance. He also knew that an underdog’s life is far easier if he gets his teeth into a match early, doing all he can to keep both his opponent and partisan fans off balance.

Djokovic accomplished this by eking out a first-set tiebreak. But the effort was so costly that he swiftly lost set two in just 25 minutes, though he rebounded by winning the third-set tiebreak. He finally broke Federer for the first time in the fourth, but still lost the set.

Djokovic was hanging on, but barely. “I thought most of the match I was on the back foot. I was defending. He was dictating the play. I just tried to fight and find a way when it mattered the most.”

It never mattered more than following a critical service break by Federer at 7-all in the fifth. The match was on his racquet at 8-7, 40-15, but Djokovic dispatched both match points. The first, with a terrific second-serve return that goaded Federer into a miss with an inside-out forehand. Next, Federer hit a mediocre approach shot that Djokovic converted into a forehand pass. Rattled, Federer made two swift forehand errors to lose serve.

Federer’s big chance had evaporated, the blown opportunities loomed large as Djokovic patiently worked his way into a final-set tiebreak (at 12-all, under Wimbledon's then-new rule) and salted it away in an anti-climax.

The irony is that Federer was the bolder, more dazzling player the entire way. He smacked 25 aces and a whopping 94 winners, a +34 advantage in the winner-to-unforced error ratio. It was also 40 more winners than the more defense-minded Djokovic hit, while tossing in 52 unforced errors of his own—just nine fewer than his risk-taking, aggressive rival.

Had he won, Federer would have become the oldest man to win a major singles title in the Open Era. Successive wins, at age 37, over Nadal and Djokovic at Wimbledon might have become the defining moment of his career. This result amounted to a two-title swing in the record book. Had Federer added No. 21, he would have prevented his rivals from adding a title. Djokovic would have remained at 15.

I just feel like it’s such an incredible opportunity missed, I can’t believe it. Roger Federer

Deflated, Federer commented:  “I just feel like it’s such an incredible opportunity missed, I can’t believe it.”

The win was Djokovic’s fourth at the previous five majors. The youngest of the Big 3, Djokovic closed to within two majors of Nadal (who had 18) and four of Federer. If you’re looking for a tipping point in the great Grand Slam singles title derby, you found it.

Finally, this match forced most observers to revisit the “Greatest Match of All-Time” honor bestowed on that 2008 Wimbledon final between Federer and Nadal. Ironically, both matches were bittersweet experiences for Federer.

When he was asked if he felt any similarity between the match he’d just lost to Djokovic and the 2008 battle with Nadal, he replied: “This one is more straightforward maybe in some ways because we didn’t have the rain delays, we didn’t have the night coming in and all that stuff. But sure, epic ending, so close, so many moments. I mean, sure there’s similarities. But you’ve got to go dig, see what they are. I’m the loser both times, so that’s the only similarity I see.”

At that moment, Federer's glass did not look half full. It seemed empty.

Honorable mention: Setting aside the storied Wimbledon loss to Nadal, and Juan Martin del Potro’s sensational upset of Federer the 2009 US Open final, we’ll give the HM nod to Andy Murray’s mastery of Federer in the gold medal match at the 2012 London Olympics. Murray upset Federer 6-2, 6-1, 6-4 on home soil ... er, grass (the tennis was held at Wimbledon).

It did not help Federer’s cause that he had to go to 19-17 in-the-third set to subdue del Potro in the semis. Thus, Federer never did complete a career Golden Slam.