Greatest Men's Matches of the 21st Century

To kick off the 2026 podcasting season the TWAA crew came up with the list of “The greatest men’s matches of the century”. This was an incredibly fun exercise with a lot of minute details and the surrounding context of these great matches. The panelists are Steve Flink, Andrew Burton, Mert Ertunga and host Saqib Ali. Get ready for this detailed unpacking of some of the best men’s matches of last 25 years. Please tag us on twitter and share your list! Lists Mert Ertunga Nadal vs Federer Rome 2006 Nadal vs Federer Wimbledon 2008 Djokovic vs Nadal Wimbledon 2018 Alcaraz vs Sinner RG 2025 Safin vs Federer AO 2005 Sampras vs Agassi USO 2001 Nadal vs Djokovic RG 2013 Djokovic vs Federer Wimbledon 2014 Rafter vs Agassi Wimbledon 2001 Djokovic vs Wawrinka AO 2013 Steve Flink Nadal vs Federer Wimbledon 2008 Djokovic vs Nadal AO 2012 Alcaraz vs Sinner RG 2025 Djokovic vs Federer Wimbledon 2019 Sampras vs Agassi USO 2001 Djokovic vs Nadal Wimbledon 2018 Nadal vs Federer Rome 2006 Safin vs Federer AO 2005 Djokovic vs Murray Shanghai 2012 Nadal vs Medvedev AO 2022 Andrew Burton Nadal vs Federer Rome 2006 Mayer vs Souza Davis Cup 2015 Nadal vs Federer Wimbledon 2008 Alcaraz vs Sinner RG 2025 Wawrinka vs Djokovic RG 2015 Djokovic vs Federer Wimbledon 2019 Nadal vs Djokovic Rg 2013 Djokovic vs Nadal Miami 2011 Federer vs Del Potro Olympics 2012 Ivanisevic vs Rafter Wimbledon 2001 Saqib Ali Nadal vs Federer Wimbledon 2008 Djokovic vs Nadal AO 2012 Djokovic vs Nadal Wimbledon 2018 Safin vs Federer AO 2005 Nadal vs Federer Rome 2006 Alcaraz vs Sinner RG 2025 Rafter vs Agassi Wimbledon 2000 Djokovic vs Federer Wimbledon 2014 Djokovic vs Wawrinka AO 2013 Safin vs Agassi AO 2004