Roger Federer's Heart-Breakers: The Matches He Might Have Won

Its often that we talk about Roger Federer's great victories, and the lightning speed with which he amassed his 13 grand slams over six odd years.

But its not often that we look, in those 237 weeks as Number One, those glorious years of the Federer era, at the disappointments, and the defeats which he suffered, in the biggest moments, which may arguably define him as the greatest ever, or be black marks in his career at the very top.

These are his defeats in semi-final or finals matches, over five sets. 

In writing this, of course, I am very aware that Roger had unbelievable victories in five set matches as No. 1, but it is remarkable that his record in five-set matches at such a level, and point in a tournament, when players are almost able to smell the trophy, between 2004 and 2009, has been 2-7.

His lone victories in these circumstances were both against, predictably, Rafael Nadal, at Miami in 2005, and at Wimbledon two years later.

In examining this unusual statistic of Federer I have not, of course, considered those five-set matches before semifinals and finals levels, simply because the Roger of the third round is simply not going to have been as hungry as the Roger in the semifinals. 

So here it is, in order of disappointment level i.e., meaningfulness to his career, I do not intend to demean the achievements of his opponents in having won these matches (No. 1 is the worst):

No. 5: David Nalbandian defeats Federer at the Shanghai Masters Cup final 2005: 6-7, 6-7, 6-2, 6-1, 7-6

A disappointing loss, because Roger had been up 6-5 in the final set, serving at 30-0, having come back from a 0-4 deficit. But he had also been with ankle trouble, and not at all in top form coming into the tournament. He would later say that he could only try to "make it difficult" for Nalbandian at the said point, serving for the match.

No. 4: Rafael Nadal defeats Federer at the Rome Masters final 2006: 6-7, 7-6, 6-4, 2-6, 7-6

This was one of the defining moments in the Federer-Nadal rivalry, one that perhaps lifted it above simply the level of man versus boy.

They had played five sets before in a final, a year ago, but not when the winner had had to save match points, and not when the intensity of the two dropped, even to the end.

Roger had two match points at 5-6, 15-40 in the fifth set, in which he had been up a break 4-1. On the first Roger missed a forehand badly, which might have made a huge impact, ultimately, on his chances at the French that year, and in making inroads to his rivalry with Nadal.

It might have been a defining moment in his GOAT status, and one which he could have won. In it we saw the first inklings of the great finals they would play the year after, up till this year, in the slams.

No. 3: Marat Safin defeats Federer at the Australian Open semifinals 2005: 5-7, 6-4, 5-7, 7-6, 9-7

This is another match, which, in the long run, might have made an impact on his GOAT status, and another one in which he had match point. That is, in that awesome fourth set breaker.

It is true, that Roger would march back from 2-5 in the fifth, and save quite a few match points, but Safin, then, at the closing ends of that match, might have been too strong. He would say four years later (this year) that he felt Roger had been too passive in the fifth, but maybe that's because he was playing unbelievable.

But still, Roger's finals streak was broken in that match, and certainly more significantly, as hindsight has shown, it killed his chance of winning three of the four slams in the same year four years in a row.

It also meant that last season's Open title might have been his record-equalling 14th.

No. 2: Rafael Nadal defeats Federer at the Wimbledon final 2008: 6-4, 6-4, 6-7, 6-7, 9-7

Another 9-7 victory in the fifth set. Copious words have been spent talking about this match.

I would not need to reiterate simply the magic, and incomparable drama of that night (I spent the whole night from 12 to 6 in Australia watching it), and moreover the historical repercussions of Nadal's victory.

It is a match Roger might also, like the last two matches in the list, have won. He had break points at 4-3 in the fifth to serve for the title, and was within two points at 5-4, 30 all.

But Nadal, maybe, in those moments was just the better. Maybe Nadal played, that day, the match of his life. And he deserved it. Perhaps, so did Roger.

History was stolen from him, the chance to win six championships in as many years, and hold a record that might have been untouchable until 2014. 

No. 1: Rafael Nadal defeats Federer at the Australian Open final 2009: 7-5, 3-6, 7-6, 3-6, 6-2

Some might wonder why I have not put the Wimbledon final of last year in this spot in the list, but that's only because I don't believe that match hurt Roger as badly as this one.

True, that was a Wimbledon, Roger's spiritual home. And yes, that might have broken a record, whereas this would only have equalled one.

But that had been something of an affirmation of the incredible dynamic that exists between Roger and Rafa, that special symphony and balance that just makes a match great to watch. It confirmed their rivalry.

This match, however, was certainly much more of a coulda woulda shoulda. Roger had many chances, 4-2 in the first set, about five break points in the third, and of course one cannot forget all the double faults.

Most uncharacteristic. Perhaps more surprising, the fading away in the third. He had it at a match at 2-sets-all, 1-2, at 30-0 in the fifth. And then it just went away, and so did his dreams.

We all know what it feels like to lose, and we all know what it feels like to have dreams and ambitions, long cherished, broken in an instant. But what does it feel like to be tormented and constantly placed aside by one man, and be second best?

These were the feelings we all read in Roger's tears that night, an in-depth examination, almost, of the human soul, in these life-defining moments. Only Roger may understand why this should be at the top of the list.

So there it is, the moments in Roger's career which, I have felt, we might all be examining in the coming months.

These were matches which Roger could have won, and which could have earned, in places, a form of immortality. But these were glories he failed to grasp.

We might think about how the world, and tennis history, might be, if Federer had won some of these.

He might have won the Australian four times in a row. He might have out-done John McEnroe in win-loss for the year in 2005. He might have broken Borg's record at Wimbledon. He might have already broken Sampras' slam record.

Maybe, in writing this, I have been too demanding, and looked too pedantically at Roger's career. But these were big losses, in big moments in tournaments.

It is true, that other champions also had heart-breakers, and, admittedly, three of the five losses have come to Nadal, but, importantly, what does this say about him? And what does this say about Roger?