clout
Hall of Fame
I feel like I did a thread like this a while back, but if so, it probably needs an update anyways. Here are some off the top of my head:
2000: Kucera def. Agassi at RG OR Clement def. Agassi at USO
2001: 19-year old Federer def. Sampras at WI
2002: Bastl def. Sampras at WI
2003: Karlovic def. Hewitt at WI
2004: Berdych def. Federer at Olympics OR 17-year old Nadal def. Federer in Miami
2005: Safin def. Federer at AO
2006: 19-year old Murray def. Federer at Cincy
2007: Canas def. Federer at IW and Miami back-to-back
2008: Tsonga def. Nadal at AO
2009: Soderling def. Nadal at RG
2010: Berdych def. Federer at WI
2011: Tsonga def. Federer at WI
2012: Rosol def. Nadal at WI
2013: Darcis def. Nadal at WI OR Stakhovsky def. Federer at WI
2014: Cilic & Nishikori def. Federer & Djokovic at USO
2015: Seppi def. Federer at AO (HM: Anderson def. Murray at USO)
2016: Querrey def. Djokovic at WI (HM: Willis def. Berankis at WI)
2017: Istomin def. Djokovic at AO (HMs: M. Zverev def. Murray at AO, Goffin def. Federer at WTF, and 18-year old Shapo def. Nadal in Montreal)
2018: Anderson def. Federer at WI (HM: Millman def. Federer at USO)
2019: Tsistipas def. Federer at AO
2020: Djokovic DQ at USO - if that doesn't count, then probably Schwartzman def. Nadal in Rome OR Senogo def. Djokovic in Vienna
2000: Kucera def. Agassi at RG OR Clement def. Agassi at USO
2001: 19-year old Federer def. Sampras at WI
2002: Bastl def. Sampras at WI
2003: Karlovic def. Hewitt at WI
2004: Berdych def. Federer at Olympics OR 17-year old Nadal def. Federer in Miami
2005: Safin def. Federer at AO
2006: 19-year old Murray def. Federer at Cincy
2007: Canas def. Federer at IW and Miami back-to-back
2008: Tsonga def. Nadal at AO
2009: Soderling def. Nadal at RG
2010: Berdych def. Federer at WI
2011: Tsonga def. Federer at WI
2012: Rosol def. Nadal at WI
2013: Darcis def. Nadal at WI OR Stakhovsky def. Federer at WI
2014: Cilic & Nishikori def. Federer & Djokovic at USO
2015: Seppi def. Federer at AO (HM: Anderson def. Murray at USO)
2016: Querrey def. Djokovic at WI (HM: Willis def. Berankis at WI)
2017: Istomin def. Djokovic at AO (HMs: M. Zverev def. Murray at AO, Goffin def. Federer at WTF, and 18-year old Shapo def. Nadal in Montreal)
2018: Anderson def. Federer at WI (HM: Millman def. Federer at USO)
2019: Tsistipas def. Federer at AO
2020: Djokovic DQ at USO - if that doesn't count, then probably Schwartzman def. Nadal in Rome OR Senogo def. Djokovic in Vienna
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