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For me it was AO 17 final, I remember screaming like crazy when Rafa broke and was up 3-1 in the 5th set, and my friend with whom I was watching the match on TV told me 'dude you're crazy, the neighbors will come knocking to check what's happening.'

Then ecstasy gave way to sheer disbelief was Rafa went on to lose all the remaining games, I was watching and wasn't even sure what was happening. After it was over I went to bed and felt sick for the whole day tomorrow.

Similar after AO 12 final though it was more like a sadness that lasts until this day. WB 18 SF was also quite painful, and USO 16 4R vs Fognini.
 

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Dirty fan you are, lolol.

2016 WB SF, I thought Fed's knee was done and he'd never do well on tour again. 2019 F, disgusting as it was, comes second.
 

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2013 RG semi, I really thought Djokovic had it while up a break in the 5th. That net touch changed everything forever...
I was terrible letargic for at least 1.5 months, didn't help that Novak lost at SW19 too.
 

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For me, it was the 2009 final at the British Open. That was one of only two times (the other being his AO 2003 QF against Younes El Aynaoui) that I remember when Andy Roddick truly showed his mettle. In the match, the styles the two players are generally associated with were reversed throughout: Roddick was the fine shotmaking artist, Federer the comparatively unrefined, ball-bashing servebot. Kudos to the latter for eking out the victory bereft of his usual grace and supreme skill, though. Still, I felt that the match could have started a fresh chapter in Roddick's career, as it was Big 3 level gameplay that he produced that day. Had he not missed the critical volley at the second set tie-break, or had the stadium not cast a particularly shaped shadow near the end of the last set, the result of the match might have been (I also think: should have been) different that day. By the way, all major tournaments should use a sun blocker that should be erected when dusk approaches, so that either the entire playing field is lit or all of it is in the shade.

The ceremony also featured the "Don't be too sad, I went through some rough ones as well, one on this court last year." / "Yeah but you had already won five!" / "I already won five, but still!" exchange, which is light and playful as compared to the lowest point (and another potential match to answer the question) in tennis ceremonies that I remember, the condescending "Very quickly, he wants to say hello [in Spanish] to his friends here and in Argentina" to Del Potro in 2008, almost denying the champion the chance to give his speech in his native tongue. At least the MC was aptly named for that one.

And, of course, the ugliest occurrence in tennis matches by an infinite margin over everything else so far was when Szeles was stabbed, and then the German courts gave the assassin... the figurative equivalent of a "good job" pat on the back instead of throwing him in the slammer for a virtual eternity for pre-planned, attempted murder. Though that one, being a women's match, does not strictly qualify here.
 

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40-15 after he lost, and todays thiem desaster during the match.

I didn't watch tennis after 40-15 for 3 month
 

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2004 W Finals Fed-Roddick

2004 USO QF Roddick-Johansson

2007 W Finals Nadal-Fed

I'd say 2011 USO F and 2012 AO F, but I was already a Zen Master at that point in time
 

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That Madrid 2014 final still haunts me. I was in the mood to smash the tv screen. I was hoping Kei would get a chance to redeem the following year when a wild Clayray appeared and derailed that train. Had Kei beaten Murray, he would have very likely also beaten Nadal in that final.

I've kinda made peace with that but it still sucks to see guys like Sock and Khachanov having masters titles to their names when Kei was robbed by an unfortunate injury.
 

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Madrid 09 SF, I had a headache after it, it was a long match too.

Most heartbroken, probably Olympics 08 SF, Nole losing on the easiest smash ever.
 

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Hingis loss to Capriati in AO 2002 :cry:
 

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2013 RG semi, I really thought Djokovic had it while up a break in the 5th. That net touch changed everything forever...
I was terrible letargic for at least 1.5 months, didn't help that Novak lost at SW19 too.
You let a tennis match between two people you don’t know ruin 1.5 months of your life? facepalm
 

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Marco Cecchinato vs Djokovic at RG 2018. Pure anguish, gutwrenching stuff.
 

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Had Dominic lot - would be last night.
Cost me a lot but the win changed it all.

40-15 stung for quite some time but I think everything eventually calms down...
 

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2013 RG semi, I really thought Djokovic had it while up a break in the 5th. That net touch changed everything forever...
I was terrible letargic for at least 1.5 months, didn't help that Novak lost at SW19 too.
Yup, I've never been so furious after the match. Fortunately no tennis match affected me so badly since then (although RG2015 final was difficult as well).
 

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Yup, I've never been so furious after the match. Fortunately no tennis match affected me so badly since then (although RG2015 final was difficult as well).
No, that disappointment I was done with after 2 days. The condescending of the Wawatards and Fedaltards-suddenly-became-Wawa-gloryhunters was a bit too much to endure, but they vanished.
 

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Alejandro Falla vs. Caio Zampieri, Medellin Challenger 2016. The match ended with Zampieri winning 7-6 6-7 6-2. I felt like my head was about to explode after this one.
 

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Karlovic-Monfils Washington 2016

One of the most obvious choke you will ever see, golden opportunity to win a 500 and he messed it up while serving for it, having not been broken the whole tournament.
 
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