Which id were the most painful losses to fellow Fed fans from his group of losses?

[Pheasant]

Fed has some tough losses. Which one was your toughest to swallow as a Fed fan? I will summarize why I think these losses were tough:

2005 AO: this snapped Fed’s record streak of 24 straight wins vs the top-10. This was also Fed’s only hard court slam loss from 2004-2007. Fed was up 5-2 in that 4th set tiebreaker. He really should have won this match. This one was a tough one to swallow

2008 AO: this match scared me. Djoker’s level was incredible in this one. Now, we had another player that was now a major threat to Fed at slams. For the first time, I became a little worried about Fed reaching 14 slam titles. This Djokovic kid played an insane match.

2008 WI: this one was the toughest for me to take. Nadal had now caught up to Fed on grass. I was now seriously worried about Fed hitting 14 slam titles.

2009 AO: Now, Nadal was a monster on hard courts. This one stung, because Nadal had now beaten Federer in 3 consecutive slam finals on 3 different surfaces.

2009 USO: At first, this one didn’t hurt so much. But this one hurt more as time passed; especially since Fed ended up stranded with only 5 USO titles.

2015 USO: for the first time in 3 years,
I was actually confident that Fed could win this title; especially since Djoker seemed a bit vulnerable in 2014 at this event. Fed was on fire heading into the final. But this match ended up being the last time that I thought that Fed had a chance at beating Djoker. This match was a bit of a funeral for me.

2018 WI: I knew Fed was done at 20 slams after this. And when Fed blew match point in the 3rd set, I actually told my wife that Fed will likely lose this match now. The memory of 40-15 in the IW final that year still smacked me like a Tyson uppercut. This match was very disappointing.

2019 WI: I expected Djokovic to win in 4 sets max. But Fed gave me a tiny amount of hope when he went up a break in the 5th set. When he had double-championship point on his own serve, I figured that Fed was going to win. A few minutes later, I knew that he’d end up losing the match. This one stung a bit, due to the momentary hope that I had.

What do you guys think?

 

[Mustard]

2019 WI: I expected Djokovic to win in 4 sets max. But Fed gave me a tiny amount of hope when he went up a break in the 5th set. When he had double-championship point on his own serve, I figured that Fed was going to win. A few minutes later, I knew that he’d end up losing the match. This one stung a bit, due to the momentary hope that I had.

What about break points at 11-11 in the fifth set?

 

[NachoGPT]

RG 2011 was the one that disappointed me most as a kid. I really wanted Fed to win. He had Nadal on the ropes too.

 

[Pheasant]

What about break points at 11-11 in the fifth set?

I honestly had given up hope by that point. Fed wasn’t coming back from that 40-15 fiasco, just like Sinner wasn’t coming back after his collapse at the 2025 FO.

 

[NatF]

It's Wimbledon 2008, not that close either.

 

[Pheasant]

That 2008 Wimbledon loss was very painful. Nadal snapped Fed’s 65 match winning streak on grass and his run of 5 straight titles. Had Federer won that, then his 2003-2009 run on grass would have been 73-0 with 7 consecutive Wimbledon titles. But unfortunately, he had to settle with a 72-1 record with 6 Wimbledon titles during those 7 years.

 

[NachoGPT]

That 2008 Wimbledon loss was very painful. Nadal snapped Fed’s 65 match winning streak on grass and his run of 5 straight titles. Had Federer won that, then his 2003-2009 run on grass would have been 73-0 with 7 consecutive Wimbledon titles. But unfortunately, he had to settle with a 72-1 record with 6 Wimbledon titles during those 7 years.

Would be best for everyone (except Nadal and his fans lol) if Fed won 08 and Roddick won 09

 

[Giocoswitch]

Not a religious Federer fan or anything but I'd assume Wimb 08 and to a lesser extent AO 09 would be the most painful for many considering what they represented more broadly (end of prime Fed and losing his kingdoms as the gap between him and Nadal on clay only seemed to be growing wider).

For as excruciating as the final defeat was for the loser, I think we can all step back and rationalise that Fed's overall run at Wimb 19 is such a moral victory for him that it can't be held in the same regard as the others where Fed winning was more the norm. But then sports-related pain isn't always rational, so feel free to correct me.

 

[MichaelNadal]

RG 2011 was the one that disappointed me most as a kid. I really wanted Fed to win. He had Nadal on the ropes too.

It's Wimbledon 2008, not that close either.

That 2008 Wimbledon loss was very painful. Nadal snapped Fed’s 65 match winning streak on grass and his run of 5 straight titles. Had Federer won that, then his 2003-2009 run on grass would have been 73-0 with 7 consecutive Wimbledon titles. But unfortunately, he had to settle with a 72-1 record with 6 Wimbledon titles during those 7 years.

 

[Mustard]

RG 2011 was the one that disappointed me most as a kid. I really wanted Fed to win. He had Nadal on the ropes too.

It was a very close match in the first 3 sets, but Federer lost the first set from 5-2 up, and went 2 sets down.

Having Nadal "on the ropes" at the French Open isn't going 2 sets down.

 

[duaneeo]

I so don't get the timing of certain threads.

 

[FlyingSaucer]

 

[RS]

Would be best for everyone (except Nadal and his fans lol) if Fed won 08 and Roddick won 09

No they say switch 09 F and 19 F and keep 08 how it is

 

[MichaelNadal]

 

[Third Serve]

1998 Basel

he never recovered from that one

 

[Im(moral) Winner]

Marseille Open Final against Rosset. Fed was two points away from winning it.
Or his first two Basel finals. After the second one could think he was never destined to win his home tournament.

 

[MichaelNadal]

I still don't see why Wimby 08 was hard for Maestronians. He had already won 5 straight lol. Would you really take such an epic Wimbledon title from Nadal? He needed that win. It's like me being upset about RG 2009. He had already won 4 and came back and won a million more, doesn't bother me at all.

 

[Mustard]

I still don't see why Wimby 08 was hard for Maestronians. He had already won 5 straight lol. Would you really take such an epic Wimbledon title from Nadal? He needed that win. It's like me being upset about RG 2009. He had already won 4 and came back and won a million more, doesn't bother me at all.

Federer in his pomp was about dominance, and Nadal broke the spell. Nadal in his pomp was about grounded routine. The emperor is supposed to dominate. The gladiator is supposed to entertain, and eventually die.

 

[Devin]

2019 WI > 2009 USO > 2008 WI > 2005 AO ~ 2009 AO > 2015 USO > 2008 AO ~ 2018 WI
From most to least painful.

 

[PilotPete]

Definitely W2019, only 1 point away and up by 2 points. W2008 was not as bad IMO, Fed had mono earlier that year and lost a lot of practice blocks that year which affected his play at Wimbledon against another elite player. Plus he was very low on confidence after the FO beating.

 

[GoatNo1]

why are USO10 and 11 not in the poll? did not hurt? fed was pretty shaken in post match interwiews

 

[MHI]

I honestly had given up hope by that point. Fed wasn’t coming back from that 40-15 fiasco, just like Sinner wasn’t coming back after his collapse at the 2025 FO.

He nearly did though, did Jannik. Broke back late in the fifth. Then again, nearly broke again in the game after 5-5 in the fifth.

 

[MHI]

Surprised Federer’s USO10, USO11, and maybe even Wimbledon v Berdych 2010 aren’t on the list.

I’d be shocked if anyone picks AO08.

 

[NachoGPT]

why are USO10 and 11 not in the poll? did not hurt? fed was pretty shaken in post match interwiews

“Confidence? Are you kidding me? Oh please.. “

 

[Gastino]

2009 AO: Now, Nadal was a monster on hard courts. This one stung, because Nadal had now beaten Federer in 3 consecutive slam finals on 3 different surfaces.

2019 WI: I expected Djokovic to win in 4 sets max. But Fed gave me a tiny amount of hope when he went up a break in the 5th set. When he had double-championship point on his own serve, I figured that Fed was going to win. A few minutes later, I knew that he’d end up losing the match. This one stung a bit, due to the momentary hope that I had.

What do you guys think?

These 2 hurt the most to me :

09 AO felt like the end of dominance, Roger was broken, this final exacerbated 08 wimby even more ...it really felt bad for a long while.

19 WI might be the toughest pill to swallow for me because it changed the course of history ...God knows how things might have gone if he got that at almost 38yo...this is the one I probably redone in my head the most.

 

[Devilito]

2019 is the only correct answer because he had 2 serves to win the title. No other loss was that close to winning a slam. Sure 2008 was important, but he already went to 5 with Rafa in 2007, and he was lucky to take it to 5 after losing the first 2 sets. AO 2009 was also close but no clear winner early on. Rafa was also on fire after his win against Verdasco, which goes down as one of the best matches in tennis history.

So it's not like Rafa was coming in playing poorly. Even the US final against Delpo, he was winning and predicted to win but he was never in a clear position to close out the match, and Delpo was on fire. Even his SF loss to Novak in 2010, after having match points. That year, Rafa was on fire on hard courts, served big, and destroyed Novak. Roger winning in 2011 against Novak doesn't guarantee him a win against Rafa in the USO final.

Roger's other losse,s such as in 2015, were just that he was a god-like dominant player, but ran into Novak at his peak, just like he ran into Rafa at his peak when he played finals at the FO. This is also what makes Roger so special. Always playing finals against the best player at their peak. While Rafa rarely played Roger at his peak on hard courts or grass during the 2004-2007 era when Roger was at his peak. Rafa was to busy getting destoryed by player like Youzney.

 

[Gastino]

2019 is the only correct answer because he had 2 serves to win the title. No other loss was that close to winning a slam. Sure 2008 was important, but he already went to 5 with Rafa in 2007, and he was lucky to take it to 5 after losing the first 2 sets. AO 2009 was also close but no clear winner early on. Rafa was also on fire after his win against Verdasco, which goes down as one of the best matches in tennis history.

So it's not like Rafa was coming in playing poorly. Even the US final against Delpo, he was winning and predicted to win but he was never in a clear position to close out the match, and Delpo was on fire. Even his SF loss to Novak in 2010, after having match points. That year, Rafa was on fire on hard courts, served big, and destroyed Novak. Roger winning in 2011 against Novak doesn't guarantee him a win against Rafa in the USO final.

Roger's other losse,s such as in 2015, were just that he was a god-like dominant player, but ran into Novak at his peak, just like he ran into Rafa at his peak when he played finals at the FO. This is also what makes Roger so special. Always playing finals against the best player at their peak. While Rafa rarely played Roger at his peak on hard courts or grass during the 2004-2007 era when Roger was at his peak. Rafa was to busy getting destoryed by player like Youzney.

Yeah i share the sentiment i didn't feel that defeated after 08 nobody thought that was it for him ...19 is the ultimate if, the last dance..

 

[Mustard]

why are USO10 and 11 not in the poll? did not hurt? fed was pretty shaken in post match interwiews

Federer said at the 2011 US Open semi final post-match presser something like "How could he (Djokovic) hit a shot like that when down match point?". I remember thinking in response "How could Djokovic NOT go for a shot like that when down match point?". I think it shows the clear difference in approach. Djokovic plays point to point in the very important moments (and thinks destiny is guiding him), while Federer does all the preparation beforehand and expects it to all come together in the match itself. Nadal plays point to point virtually every point, grounded down in routines and hard work to win every point.

Federer also said in that presser "It could have been worse. It could have been a final". Ouch!

 

[MichaelNadal]

Federer said at the 2011 US Open semi final post-match presser something like "How could he (Djokovic) hit a shot like that when down match point?". I remember thinking in response "How could Djokovic NOT go for a shot like that when down match point?". I think it shows the clear difference in approach. Djokovic plays point to point in the very important moments (and thinks destiny is guiding him), while Federer does all the preparation beforehand and expects it to all come together in the match itself. Nadal plays point to point virtually every point, grounded down in routines and hard work to win every point.

Federer also said in that presser "It could have been worse. It could have been a final". Ouch!

The trilogy of 40-15's is crazy

 

[Mustard]

The trilogy of 40-15's is crazy

And another one at 2006 Rome against Nadal.

 

[ALCARAZWON]

Does Djokovic usually go for clean winners that hit the outside edge of the line on match points?
I can't remember his tactics on match points other than vs. Federer @ USO, but I know in tiebreakers Djokovic is known for not taking risks but rather outlasting his opponents in long rallies.
Federer probably thought Djokovic was going to play error-free tennis on match point the way he does in tiebreakers...

 

[Mustard]

Does Djokovic usually go for clean winners that hit the outside edge of the line on match points?
I can't remember his tactics on match points other than vs. Federer @ USO, but I know in tie-breakers Djokovic is known for not taking risks and just outlasting his opponents in long rallies.
Federer probably thought Djokovic was going to play error-free tennis on match point the way he does in tiebreakers...

Federer's tiebreaks in the 2019 Wimbledon final were all poor. The first set tiebreak Federer actually had a lead and blew it with errors. The third and fifth set tiebreaks were more flat by Federer.

 

[Sephiroth]

it's funny seeing Wimbledon 08 being chosen after all these years instead of 19

a match where he was 2 sets down already against a far in-form and better player on that day vs a match where he had 2 match points, all the stats in his favour, and a great breakpoint conversion for Federer's standards against a choppy as hell Djokovic.

like if people actually watched these 2 matches with their eyes they would know Nadal was the far deserving winner of Wimb 08, compared to Novak with Wimb 19 but to this day some Federer fans still resent that Wimbledon 08 loss.

Nadal won Wimbledon 08
Federer lost Wimbledon 19

deal with it.

 

[helterskelter]

1998 Basel

he never recovered from that one

Can't see how he would have done, either. There's really no excuse for a young lad who's only just exited his Peak and might well still be Prime or at least Prime-ish losing to an OLD man of 28 and a half!

 

[MeatTornado]

No offense, but I flat out don't believe anyone who doesn't say 2019.

 

[BauerAlmeida]

I know all those are slams, but I figure Rome 2006 and YEC 2005 are also painful for different reasons. The former, because it was a chance to beat Nadal Bo5, the latter because he could have won 5 titles in a row at the event, if future results stay the same.

I still don't see why Wimby 08 was hard for Maestronians. He had already won 5 straight lol. Would you really take such an epic Wimbledon title from Nadal? He needed that win. It's like me being upset about RG 2009. He had already won 4 and came back and won a million more, doesn't bother me at all.

Agreed. After so many victories in a row, he had to lose again at some point. Also, he was 0-2 down, and it looked like it was going to be a routine loss.

Not only Nadal fans doesn't see to bothered about RG 2009 compared to others, same for Djokovic fans when he lost at the AO to Wawrinka or Sinner.

 

[darthrafa]

it has to be the final final at sw19
he knew this would be his last chance
one ace out of two chances will finish it
serve is main weapon at his garden and then
the rest is history and end of history of his slam run

 

[gamelovergold]

2019 must be on top.
That was his last opportunity to seal the deal but he just failed.

 

[Pheasant]

2019 is in 2nd place for me. The reason that it’s not in first is because none of us gave Federer a chance at bagging his 9th Wimbledon title at nearly 38 years of age against a guy that he hadn’t beaten at a slam in 7 years. Now granted, it sucked getting a flicker of hope when it was 40-15. But prior to that, Djoker was winning that match all along. With 2008, Federer was a coin-flip to win that match. And losing that match at just shy of being 27 years old(still in his prime) was far more damaging than losing a match as a very old man. Also, no streaks were broken in 2019. Fed already proved that he could blow a 2-set lead and match point against Kevin frickin’ Anderson the year before at Wimbledon. Whereas in 2008, the legendary streaks that I mentioned before were snapped. In addition, we all knew that this loss to Nadal meant Fed’s legendary streak of weeks at #1 was going to end in the near future with that tough 5-set loss.

I really thought that Fed was going to pull out that 2008 match after he leveled it at 2-2. And this isn’t meant to take anything away from Nadal. Rafa battled like a warrior in the 5th set. It’s almost like Rafa was thinking the following “this Federer guy is now showing us why he won 65 straight matches on grass; which incudes the last 5 Wimbledon titles. But he’s never fought a junkyard dog to the death before. He’s about to find out what that’s like.” I will give credit where credit is due. Rafa was a monster in that 5th set. That took some serious balls to stop Fed’s momentum after he had just won the previous 2 sets to force a 5th set. Nadal earned that one fair and square.

Theres a reason why many experts call that 2008 WI final the greatest match of all time. This was a passing of the torch match. Nadal had just slayed perhaps the biggest giant of all time(up to that point) by gutting out a 5-setter on Fed’s best surface. This was a very sad day for us Fed fans, even though he couldn’t have lost to a classier guy(Nadal was always all class).

 

[GrassMasters]

What a choker

 

[Mustard]

2019 is in 2nd place for me. The reason that it’s not in first is because none of us gave Federer a chance at bagging his 9th Wimbledon title at nearly 38 years of age against a guy that he hadn’t beaten at a slam in 7 years. Now granted, it sucked getting a flicker of hope when it was 40-15. But prior to that, Djoker was winning that match all along.

Federer basically dominated play in the 2019 Wimbledon final up to leading 5-1 in the fourth set. The only bad spell was blowing a lead in the first set tiebreak, and playing a flat third set tiebreak. After Federer led 5-1 in the fourth set, it got more complicated, but in the match overall Federer was clearly the better player for most of it, but played 3 poor tiebreaks that cost him.

 

[Razer]

2009 Aus Open was by far the worst loss of Federer, especially given how Federer was crying in the end, it was the slam where his dominance on all 3 surfaces was ended by Nadal by beating him in the last 10 months in slams on all 3 surfaces.

Federer crying was the most disgusting sign for his fans and haters like, it was awkward. You had to witness it live to know how pathetic it was.

 

[NachoGPT]

2009 Aus Open was by far the worst loss of Federer, especially given how Federer was crying in the end, it was the slam where his dominance on all 3 surfaces was ended by Nadal by beating him in the last 10 months in slams on all 3 surfaces.

Federer crying was the most disgusting sign for his fans and haters like, it was awkward. You had to witness it live to know how pathetic it was.

I think Fed probably thought in that moment that he was done and would never win a slam again or beat Nadal again. He did well to recover from it and win RG + Wimbledon that year. Many would have collapsed completely.

 

[Razer]

I think Fed probably thought in that moment that he was done and would never win a slam again or beat Nadal again. He did well to recover from it and win RG + Wimbledon that year. Many would have collapsed completely.

Federer got lucky with Nadal's body collapsing in the clay season. His journey from 13 to 15 was gonna become a nightmare if Nadal had not got injured and he would never have won the french too.

09AO hit harder than 08W and that hit harder than 19W which obviously hit harder than others in that sequence. 08W was pretty big shock when it came but 09AO topped it with Fed crying and all that, making it a very bad day for everyone, even the Nadal fanbase was feeling bad and disgusted after seeing what they witnessed.

 

[GoatNo1]

must be the most painful trilogy

 

[Razer]

must be the most painful trilogy

Nobody cares much for all this. Not as much as the losses to Nadal in 08-09.

 

[GoatNo1]

Does Djokovic usually go for clean winners that hit the outside edge of the line on match points?
I can't remember his tactics on match points other than vs. Federer @ USO, but I know in tiebreakers Djokovic is known for not taking risks but rather outlasting his opponents in long rallies.
Federer probably thought Djokovic was going to play error-free tennis on match point the way he does in tiebreakers...

did you sow his TBs in OG final? as razs fan you surely wshould

 

[GoatNo1]

Nobody cares much for all this. Not as much as the losses to Nadal in 08-09.

still, only W option (not counting the other 2 there he was pretty salty in post match interviews) has 65% of votes!

 

[Razer]

still, only W option (not counting the other 2 there he was pretty salty in post match interviews) has 65% of votes!

Recency bias has 2019W in mind of people but those who saw tennis from the 2000s know that 2019W was not that much of a bad as people remember now. He was a loser in the past too from MP, it was not the end of the world in 2019W because worse defeats had happened in the past.

 

[Hitman]

I felt BAD for Federer after W 2019, and I was cheering the other guy throughout that match. So If I felt that way, I can only imagine how devastating that was for Federer fans. Kind of like how Federer fans felt bad for Roddick after W 2009, they knew how devastating that was Roddick.

How W 2019 cannot be the one that tops the list, I don't know. It was the toughest loss of his career IMO, no question about it for me.