Winner Sinner
Hall of Fame
Federer 2004
Roland Garros eliminated in the third round by Kuerten 4-6 4-6 4-6
Federer 2006
Roland Garros eliminated in the final by Nadal 6-1 1-6 4-6 6-7
Federer 2007
Roland Garros eliminated in the final by Nadal 3-6 6-4 3-6 4-6
Nadal 2010
Australian Open eliminated in the quarterfinals by Murray due to retirement (3-6 6-7 0-3)
Djokovic 2011
Roland Garros eliminated in the semifinals by Federer 6-7 3-6 6-3 6-7
Djokovic 2015
Roland Garros eliminated in the final by Wawrinka 6-4 4-6 3-6 4-6
Djokovic 2021
Us Open eliminated in the final by Medvedev 4-6 4-6 4-6
Djokovic 2023
Wimbledon eliminated in the final by Alcaraz 6-1 6-7 1-6 6-3 4-6
I say in hindsight Djokovic 2023, he should have won that final with Alcaraz because he was still the strongest on the surface.
While the 2021 final with Medvedev at the US Open was already cooked after the extra efforts at the Tokyo Olympics.
But in the end I vote Roland Garros 2004.
Before Nadal opened his reign on clay and at Roland Garros, Federer had the great opportunity to win Roland Garros and compile the CYGS precisely in 2004.
The Federer 2005, 2006, 2007, surely would have won that edition of Roland Garros.
Instead he was eliminated prematurely by a declining Kuerten.
Roland Garros eliminated in the third round by Kuerten 4-6 4-6 4-6
Federer 2006
Roland Garros eliminated in the final by Nadal 6-1 1-6 4-6 6-7
Federer 2007
Roland Garros eliminated in the final by Nadal 3-6 6-4 3-6 4-6
Nadal 2010
Australian Open eliminated in the quarterfinals by Murray due to retirement (3-6 6-7 0-3)
Djokovic 2011
Roland Garros eliminated in the semifinals by Federer 6-7 3-6 6-3 6-7
Djokovic 2015
Roland Garros eliminated in the final by Wawrinka 6-4 4-6 3-6 4-6
Djokovic 2021
Us Open eliminated in the final by Medvedev 4-6 4-6 4-6
Djokovic 2023
Wimbledon eliminated in the final by Alcaraz 6-1 6-7 1-6 6-3 4-6
I say in hindsight Djokovic 2023, he should have won that final with Alcaraz because he was still the strongest on the surface.
While the 2021 final with Medvedev at the US Open was already cooked after the extra efforts at the Tokyo Olympics.
But in the end I vote Roland Garros 2004.
Before Nadal opened his reign on clay and at Roland Garros, Federer had the great opportunity to win Roland Garros and compile the CYGS precisely in 2004.
The Federer 2005, 2006, 2007, surely would have won that edition of Roland Garros.
Instead he was eliminated prematurely by a declining Kuerten.