Toughest loss for each big 3 member every season (from first slam final season onward)

clout

Hall of Fame
Federer:

2003 - Montreal vs Roddick
2004 - Olympics vs Berdych
2005 - AO vs Safin
2006 - RG vs Nadal
2007 - RG vs Nadal
2008 - WI vs Nadal
2009 - AO vs Nadal
2010 - USO vs Djokovic
2011 - USO vs Djokovic
2012 - WTF vs Djokovic or Olympics vs Murray
2013 - AO vs Murray
2014 - WI vs Djokovic
2015 - WI/USO vs Djokovic
2016 - WI vs Raonic
2017 - WTF vs Goffin
2018 - WI vs Anderson
2019 - WI vs Djokovic
2020 - N/A

Nadal:

2005 - Miami vs Federer
2006 - Not sure
2007 - WI vs Federer
2008 - USO vs Murray
2009 - RG vs Soderling
2010 - WTF vs Federer
2011 - WI/USO vs Djokovic
2012 - AO vs Djokovic
2013 - WTF vs Djokovic
2014 - AO vs Wawrinka
2015 - USO vs Fognini
2016 - Olympics vs Del Potro
2017 - AO vs Federer
2018 - WI vs Djokovic
2019 - AO vs Djokovic
2020 - WTF vs Medvedev

Djokovic:

2007 - USO vs Federer
2008 - Olympics vs Nadal
2009 - Madrid vs Nadal
2010 - AO vs Tsonga
2011 - RG vs Federer
2012 - RG vs Nadal
2013 - RG vs Nadal
2014 - AO vs Wawrinka or RG vs Nadal
2015 - RG vs Wawrinka
2016 - Olympics vs Del Potro
2017 - AO vs Istomin
2018 - WTF vs Zverev or RG vs Cechinnato
2019 - RG vs Thiem
2020 - USO DQ
 
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Garro

Rookie
Good thread! I agree with most of the picks with a few exceptions.

Nadal: 2006 would still have to be Wimbledon as that was the only final he lost; 2011 Wimbledon too as he was the favorite in that match, not so much in the US Open.

Fed has talked about that 2009 US Open loss being one of the most difficult of his career, even though the AO seemed to be much more emotional for him at the time.
He never seemed that bothered by the 2010 US Open loss (in stark contrast to 2011), but at the same time I'm not sure there's another loss that would eclipse it that year.

Djokovic I lean toward RG for 2014. He was very bitter in the press conference and, unusually for him, did not give much credit to Rafa even though he played some fabulous tennis at least in spurts.
He also considered quitting tennis after losing 2010 RG up two sets to love to Melzer so that would have to be the toughest for that year.
 
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lud

Hall of Fame
2006 for Fed has to be Rome
2009 is USO. Sure, AO was apsolutely tough but USO Hurt more by today's point of view.

Djoker 2012 was Olympics vs Murray

Nadal 2015 was RG vs Djokovic
2006 is Wimbledon probably
 

abmk

Bionic Poster
Fed:

2003 - USO vs Nalby 1st (other 2: Montreal semi and Horna RG 1R)
2004 - RG vs Kuerten (berdych loss in Oly the 2nd one)
2005 - RG vs nadal/AO vs Safin (AO was tougher in that he was so close to wining, RG tougher in that he could've played clearly better to have a shot at winning; 3rd one: YEC final vs Nalby)
2006 - Rome final vs Nadal, RG final vs Nadal (RG final would've given him win vs nadal at RG and a shot at CYGS, Rome final obviously so close and had some effect at RG)
2007 - RG final vs Nadal
2008 - Wim final vs Nadal/RG final vs Nadal (for losing that badly at RG)
2009 - AO final vs Nadal (USO final vs delpo 2nd)
2010 - USO semi vs Djoko
2011 - USO semi vs Djoko
2012 - USO QF vs Berdych (one-off match, else would've had a decent shot at the USO trophy), WTF 2012 final 2nd, AO 12 semi vs nadal 3rd
2013 - Wim 2R vs Stakhovsky
2014 - Wim F vs Djokovic
2015 - USO F vs Djokovic
2016 - Wim SF vs Raonic
2017 - WTF vs Goffin
2018 - Wim QF vs Anderson
2019 - Wim F vs Djokovic

Nadal:

2005 - Miami final vs Fed
2006 - Wim final vs Fed (madrid loss vs Berdych - home ground?)
2007 - Wim final vs Fed
2008 - USO SF vs Murray
2009 - RG 4R vs Soderling
2010 - AO QF vs Murray (WTF final vs fed next)
2011 - Wim F vs Djokovic (Rome Final and Miami final next 2)
2012 - AO F vs Djoko (Wim 2R vs Rosol next)
2013 - Wim 1R vs Darcis
2014 - AO F vs Stan (Wim 4R vs Kyrgios next)
2015 - RG QF vs Djoko/USO 3R vs Fog
2016 - Oly vs delpo
2017 - AO F vs fed
2018 - Wim SF vs djoko
2019 - AO F vs djoko
2020 - YEC SF vs med

Djokovic:

2007 - USO F vs Fed
2008 - Oly SF vs Nadal
2009 - Madrid SF vs Nadal/RG 3R vs Kohl
2010 - RG QF vs Melzer (from up 2 sets to love)
2011 - RG SF vs Fed
2012 - USO F vs Murray
2013 - RG SF vs Nadal/USO F vs Nadal
2014 - USO SF vs Nishi/AO QF vs Stan (RG F vs Nadal 3rd IMO)
2015 - RG F vs Stan
2016 - Querrey at Wim/Wawr at USO/Delpo at Oly/Murray at WTF
2017 - Istomin at AO
2018 - Cecchinatto at AO/Zverev in WTF final
2019 - USO vs wawr(?)/thiem at WTF/thiem at RG
2020 - USO DQ vs PCB/Nadal RG final
 
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