Match log updated: 2026-05-28 18:14 UTC
Justin Gimelstob — ATP Match Log
Main draw matches: 278 | W: 107 | L: 171 | Win %: 38.5%
18 qualifying matches shown below; qualifying is excluded from main-draw summaries and leaderboards.
| Date ↓ | Tournament | Category | Round | Surface | Opponent | Score | Result | H2H | Match |
|---|---|---|---|---|---|---|---|---|---|
| Oct 25, 2007* | St. Petersburg | ATP 250 | R32 | Carpet | Mikhail Youzhny | 2-6 4-6 | L | H2H | Match data |
| Oct 11, 2007* | Moscow | ATP 250 | R32 | Hard | Philipp Kohlschreiber | 1-6 3-6 | L | H2H | Match data |
| Oct 4, 2007* | Tokyo | ATP 500 | R32 | Hard | Thomas Johansson | 4-6 4-6 | L | H2H | Match data |
| Oct 3, 2007* | Tokyo | ATP 500 | R64 | Hard | Lukasz Kubot | 6-4 7-5 | W | H2H | Match data |
| Aug 29, 2007* | US Open | Grand Slam | R128 | Hard | Andy Roddick | 6-7(6) 3-6 3-6 | L | H2H | Match data |
| Jul 23, 2007 | Indianapolis | ATP 250 | R32 | Hard | Evgeny Korolev | 2-6 4-6 | L | H2H | Match data |
| Jul 12, 2007* | Newport | ATP 250 | R32 | Grass | Vincent Spadea | 4-6 3-6 | L | H2H | Match data |
| Jun 27, 2007* | Wimbledon | Grand Slam | R128 | Grass | Andy Roddick | 1-6 5-7 6-7(3) | L | H2H | Match data |
| Jun 21, 2007* | Nottingham | ATP 250 | R32 | Grass | Amer Delic | 4-6 4-6 | L | H2H | Match data |
| Jun 19, 2007* | Nottingham | ATP 250 | Q3 | Grass | Ken Skupski | 6-4 6-7(3) 6-3 | W | H2H | Match data |
| Jun 18, 2007 | Nottingham | ATP 250 | Q2 | Grass | Ian Flanagan | 6-4 6-3 | W | H2H | Match data |
| Jun 18, 2007 | Nottingham | ATP 250 | Q1 | Grass | Alexander Reichel | 3-6 6-3 6-4 | W | H2H | Match data |
| Jun 13, 2007* | Queen's Club | ATP 500 | R64 | Grass | Jonas Bjorkman | 3-6 6-3 1-6 | L | H2H | Match data |
| May 30, 2007* | Roland Garros | Grand Slam | R128 | Clay | Nicolas Almagro | 4-6 4-6 4-6 | L | H2H | Match data |
| Apr 12, 2007* | Houston | ATP 250 | R32 | Clay | Nicolas Devilder | 2-6 3-6 | L | H2H | Match data |
| Mar 7, 2007* | Indian Wells Masters | Masters 1000 | R128 | Hard | Daniele Bracciali | 2-6 1-6 | L | H2H | Match data |
| Sep 1, 2006* | US Open | Grand Slam | R64 | Hard | David Ferrer | 2-6 4-6 1-6 | L | H2H | Match data |
| Aug 30, 2006* | US Open | Grand Slam | R128 | Hard | Oliver Marach | 6-2 6-3 7-5 | W | H2H | Match data |
| Aug 23, 2006* | New Haven | ATP 250 | R64 | Hard | Gilles Simon | 6-4 5-7 1-6 | L | H2H | Match data |
| Aug 17, 2006* | Cincinnati Masters | Masters 1000 | R32 | Hard | Robin Soderling | 3-6 6-2 6-7(6) | L | H2H | Match data |
| Aug 16, 2006* | Cincinnati Masters | Masters 1000 | R64 | Hard | Feliciano Lopez | 6-3 7-6(4) | W | H2H | Match data |
| Aug 2, 2006* | Washington | ATP 250 | R64 | Hard | Ryan Sweeting | 6-7(7) 2-6 | L | H2H | Match data |
| Jul 27, 2006* | Los Angeles | ATP 250 | R32 | Hard | Robby Ginepri | 4-6 4-6 | L | H2H | Match data |
| Jul 17, 2006 | Indianapolis | ATP 250 | R64 | Hard | Wesley Whitehouse | 3-6 5-7 | L | H2H | Match data |
| Jul 16, 2006* | Newport | ATP 250 | F | Grass | Mark Philippoussis | 3-6 5-7 | L | H2H | Match data |
| Jul 15, 2006* | Newport | ATP 250 | SF | Grass | Andy Murray | 6-1 7-6(4) | W | H2H | Match data |
| Jul 15, 2006* | Newport | ATP 250 | QF | Grass | Kristian Pless | 6-3 6-1 | W | H2H | Match data |
| Jul 14, 2006* | Newport | ATP 250 | R16 | Grass | Wayne Arthurs | 6-3 7-6(1) | W | H2H | Match data |
| Jul 13, 2006* | Newport | ATP 250 | R32 | Grass | Wesley Whitehouse | 4-6 6-3 6-4 | W | H2H | Match data |
| Jun 30, 2006* | Wimbledon | Grand Slam | R64 | Grass | Ivan Ljubicic | 3-6 6-7(1) 5-7 | L | H2H | Match data |
| Jun 28, 2006* | Wimbledon | Grand Slam | R128 | Grass | Christophe Rochus | 6-3 6-4 6-4 | W | H2H | Match data |
| Jun 22, 2006* | Nottingham | ATP 250 | R32 | Grass | Robin Soderling | 6-7(5) 7-6(4) 6-7(7) | L | H2H | Match data |
| Jun 15, 2006* | Queen's Club | ATP 250 | R32 | Grass | James Blake | 5-7 1-6 | L | H2H | Match data |
| Jun 14, 2006* | Queen's Club | ATP 250 | R64 | Grass | Raemon Sluiter | 7-6(7) 6-2 | W | H2H | Match data |
| May 31, 2006* | Roland Garros | Grand Slam | R128 | Clay | Alejandro Falla | 4-6 4-6 2-6 | L | H2H | Match data |
| May 6, 2006* | Estoril | ATP 250 | QF | Clay | Albert Portas | 4-6 3-6 | L | H2H | Match data |
| May 5, 2006* | Estoril | ATP 250 | R16 | Clay | Nicolas Massu | 2-6 7-6(3) 6-4 | W | H2H | Match data |
| May 4, 2006* | Estoril | ATP 250 | R32 | Clay | Lukas Dlouhy | 3-6 7-5 6-3 | W | H2H | Match data |
| Apr 26, 2006* | Barcelona | ATP 250 | R64 | Clay | Agustin Calleri | 2-6 1-6 | L | H2H | Match data |
| Mar 21, 2006* | Miami Masters | Masters 1000 | R128 | Hard | Paul Goldstein | 6-3 6-7(6) 1-1 (ret.) | L | H2H | Match data |
| Mar 8, 2006* | Indian Wells Masters | Masters 1000 | R64 | Hard | David Nalbandian | 4-6 4-6 | L | H2H | Match data |
| Mar 7, 2006* | Indian Wells Masters | Masters 1000 | R128 | Hard | Feliciano Lopez | 7-5 6-3 | W | H2H | Match data |
| Feb 23, 2006* | Memphis | ATP 250 | R32 | Hard | Tommy Haas | 1-2 (ret.) | L | H2H | Match data |
| Feb 17, 2006* | San Jose | ATP 250 | R16 | Hard | Kristof Vliegen | 6-7(1) 6-4 1-6 | L | H2H | Match data |
| Feb 16, 2006* | San Jose | ATP 250 | R32 | Hard | Bjorn Rehnquist | 6-1 6-4 | W | H2H | Match data |
| Feb 3, 2006* | Delray Beach | ATP 250 | R16 | Hard | Xavier Malisse | 2-6 5-7 | L | H2H | Match data |
| Feb 2, 2006* | Delray Beach | ATP 250 | R32 | Hard | Danai Udomchoke | 6-4 6-4 | W | H2H | Match data |
| Jan 18, 2006* | Australian Open | Grand Slam | R128 | Hard | Marcos Baghdatis | 6-7(6) 5-7 0-6 | L | H2H | Match data |
| Jan 6, 2006* | Chennai | ATP 250 | R16 | Hard | Carlos Moya | 6-3 3-6 4-6 | L | H2H | Match data |
| Jan 5, 2006* | Chennai | ATP 250 | R32 | Hard | Alexander Waske | 6-2 6-2 | W | H2H | Match data |
| Oct 5, 2005* | Tokyo | ATP 250 | R64 | Hard | Alexander Waske | 6-3 6-7(5) 6-7(3) | L | H2H | Match data |
| Sep 30, 2005* | Bangkok | ATP 250 | R16 | Hard | Lleyton Hewitt | 4-6 7-5 6-7(9) | L | H2H | Match data |
| Sep 29, 2005* | Bangkok | ATP 250 | R32 | Hard | Nicolas Lapentti | 6-4 6-3 | W | H2H | Match data |
| Sep 16, 2005* | Beijing | ATP 250 | R16 | Hard | Rafael Nadal | 7-5 4-6 4-6 | L | H2H | Match data |
| Sep 15, 2005* | Beijing | ATP 250 | R32 | Hard | Roko Karanusic | 6-4 6-1 | W | H2H | Match data |
| Aug 31, 2005* | US Open | Grand Slam | R128 | Hard | Max Mirnyi | 2-6 5-7 2-6 | L | H2H | Match data |
| Aug 25, 2005* | New Haven | ATP 250 | R32 | Hard | Fernando Gonzalez | 2-6 6-3 4-6 | L | H2H | Match data |
| Aug 24, 2005* | New Haven | ATP 250 | R64 | Hard | Guillermo Garcia-Lopez | 3-6 7-5 7-6(4) | W | H2H | Match data |
| Jun 26, 2005* | Wimbledon | Grand Slam | R32 | Grass | Lleyton Hewitt | 6-7(5) 4-6 5-7 | L | H2H | Match data |
| Jun 24, 2005* | Wimbledon | Grand Slam | R64 | Grass | Nicolas Massu | 6-3 4-6 7-6(5) 7-6(0) | W | H2H | Match data |
| Jun 22, 2005* | Wimbledon | Grand Slam | R128 | Grass | Adrian Garcia | 6-3 6-4 7-6(5) | W | H2H | Match data |
| Jun 21, 2005* | Wimbledon | Grand Slam | Q3 | Grass | George Bastl | 0-1 (ret.) | L | H2H | Match data |
| Jun 21, 2005* | Wimbledon | Grand Slam | Q2 | Grass | Vladimir Voltchkov | 6-4 0-6 6-3 | W | H2H | Match data |
| Jun 20, 2005 | Wimbledon | Grand Slam | Q1 | Grass | Victor Ionita | 6-3 6-2 | W | H2H | Match data |
| Feb 25, 2005* | Scottsdale | ATP 250 | R16 | Hard | Wayne Arthurs | 2-6 7-6(5) 6-7(6) | L | H2H | Match data |
| Feb 24, 2005* | Scottsdale | ATP 250 | R32 | Hard | Kristof Vliegen | 6-3 7-6(3) | W | H2H | Match data |
| Jan 19, 2005* | Australian Open | Grand Slam | R128 | Hard | Gaston Gaudio | 6-7(3) 4-6 3-6 | L | H2H | Match data |
| Jan 8, 2005* | Chennai | ATP 250 | QF | Hard | Tomas Zib | 3-6 6-7(4) | L | H2H | Match data |
| Jan 7, 2005* | Chennai | ATP 250 | R16 | Hard | Jonas Bjorkman | 6-0 4-6 6-3 | W | H2H | Match data |
| Jan 6, 2005* | Chennai | ATP 250 | R32 | Hard | Jan-Michael Gambill | 6-3 6-3 | W | H2H | Match data |
| Oct 7, 2004* | Tokyo | ATP 250 | R32 | Hard | Thomas Johansson | 4-6 4-6 | L | H2H | Match data |
| Oct 6, 2004* | Tokyo | ATP 250 | R64 | Hard | Christophe Rochus | 6-6(2) (ret.) | W | H2H | Match data |
| Sep 30, 2004* | Bangkok | ATP 250 | R32 | Hard | Taylor Dent | 6-4 4-6 4-6 | L | H2H | Match data |
| Sep 16, 2004* | Beijing | ATP 250 | R32 | Hard | Juan Carlos Ferrero | 4-6 1-6 | L | H2H | Match data |
| Aug 30, 2004 | US Open | Grand Slam | Q1 | Hard | Tuomas Ketola | 3-6 6-3 5-7 | L | H2H | Match data |
| Aug 19, 2004* | Washington | ATP 250 | R32 | Hard | Alejandro Falla | 6-3 4-6 3-6 | L | H2H | Match data |
| Jul 8, 2004* | Newport | ATP 250 | R32 | Grass | Cyril Saulnier | 1-6 6-3 1-6 | L | H2H | Match data |
| Jun 22, 2004* | Wimbledon | Grand Slam | Q3 | Grass | Ramon Delgado | 6-2 0-6 2-6 4-6 | L | H2H | Match data |
| Jun 22, 2004* | Wimbledon | Grand Slam | Q2 | Grass | Jean Francois Bachelot | 6-3 3-6 6-2 | W | H2H | Match data |
| Jun 21, 2004 | Wimbledon | Grand Slam | Q1 | Grass | Juan-Pablo Guzman | 6-3 6-2 | W | H2H | Match data |
| Oct 1, 2003* | Tokyo | ATP 250 | R64 | Hard | Cyril Saulnier | 6-7(5) 6-3 1-6 | L | H2H | Match data |
| Sep 26, 2003* | Shanghai | ATP 250 | R16 | Hard | Robin Soderling | 4-6 4-6 | L | H2H | Match data |
| Sep 25, 2003* | Shanghai | ATP 250 | R32 | Hard | Alexander Waske | 6-3 7-6(4) | W | H2H | Match data |
| Aug 27, 2003* | US Open | Grand Slam | R128 | Hard | Dominik Hrbaty | 3-6 4-6 2-6 | L | H2H | Match data |
| Jul 31, 2003* | Los Angeles | ATP 250 | R32 | Hard | Vincent Spadea | 4-6 3-6 | L | H2H | Match data |
| Jul 21, 2003 | Indianapolis | ATP 250 | R32 | Hard | Alex Bogomolov Jr | 2-6 4-6 | L | — | Match data |
| Jul 12, 2003* | Newport | ATP 250 | QF | Grass | Gregory Carraz | 6-2 1-6 6-7(3) | L | H2H | Match data |
| Jul 11, 2003* | Newport | ATP 250 | R16 | Grass | Zack Fleishman | 1-6 6-3 6-3 | W | H2H | Match data |
| Jul 10, 2003* | Newport | ATP 250 | R32 | Grass | Jeff Morrison | 6-4 4-6 7-6(13) | W | H2H | Match data |
| Jun 29, 2003* | Wimbledon | Grand Slam | R32 | Grass | Jonas Bjorkman | 1-6 3-6 3-6 | L | H2H | Match data |
| Jun 27, 2003* | Wimbledon | Grand Slam | R64 | Grass | Arnaud Clement | 2-6 6-3 6-4 6-7(2) 6-1 | W | H2H | Match data |
| Jun 25, 2003* | Wimbledon | Grand Slam | R128 | Grass | Irakli Labadze | 6-2 6-2 6-4 | W | H2H | Match data |
| Jun 19, 2003* | Nottingham | ATP 250 | R32 | Grass | Vladimir Voltchkov | 1-6 5-7 | L | H2H | Match data |
| Jun 11, 2003* | Queen's Club | ATP 250 | R64 | Grass | Ivo Karlovic | 6-7(4) 6-4 6-7(3) | L | H2H | Match data |
| May 28, 2003* | Roland Garros | Grand Slam | R128 | Clay | Mariano Puerta | 2-6 6-4 6-7(1) 1-6 | L | H2H | Match data |
| Apr 24, 2003* | Houston | ATP 250 | R32 | Clay | Fernando Meligeni | 2-6 4-6 | L | H2H | Match data |
| Mar 7, 2003* | Delray Beach | ATP 250 | R16 | Hard | Jan-Michael Gambill | 5-7 5-7 | L | H2H | Match data |
| Mar 6, 2003* | Delray Beach | ATP 250 | R32 | Hard | Alex Bogomolov Jr | 6-4 6-0 | W | — | Match data |
| Feb 27, 2003* | Copenhagen | ATP 250 | R32 | Hard | Karol Beck | 4-6 3-6 | L | H2H | Match data |
| Feb 20, 2003* | Memphis | ATP 250 | R32 | Hard | Hyung-Taik Lee | 3-6 4-6 | L | H2H | Match data |
| Feb 15, 2003* | San Jose | ATP 250 | SF | Hard | Davide Sanguinetti | 4-6 7-6(2) 3-6 | L | H2H | Match data |
| Feb 15, 2003* | San Jose | ATP 250 | QF | Hard | Kenneth Carlsen | 6-3 6-4 | W | H2H | Match data |
| Feb 14, 2003* | San Jose | ATP 250 | R16 | Hard | Zack Fleishman | 6-1 6-4 | W | H2H | Match data |
| Feb 13, 2003* | San Jose | ATP 250 | R32 | Hard | Paradorn Srichaphan | 7-5 6-2 | W | H2H | Match data |
| Jan 15, 2003* | Australian Open | Grand Slam | R128 | Hard | Younes El Aynaoui | 6-2 6-4 4-6 0-1 (ret.) | L | H2H | Match data |
| Jan 2, 2003* | Chennai | ATP 250 | R32 | Hard | Karol Kucera | 6-3 6-7(3) 3-6 | L | H2H | Match data |
| Aug 30, 2002* | US Open | Grand Slam | R64 | Hard | Andre Agassi | 0-6 1-6 1-6 | L | H2H | Match data |
| Aug 28, 2002* | US Open | Grand Slam | R128 | Hard | Edwin Kempes | 6-4 3-6 6-3 6-7(4) 6-3 | W | H2H | Match data |
| Aug 15, 2002* | Washington | ATP 250 | R32 | Hard | Andy Roddick | 2-6 2-6 | L | H2H | Match data |
| Aug 14, 2002* | Washington | ATP 250 | R64 | Hard | Kenneth Carlsen | 6-3 6-3 | W | H2H | Match data |
| Jul 25, 2002* | Los Angeles | ATP 250 | R32 | Hard | Nicolas Kiefer | 5-7 1-6 | L | H2H | Match data |
| Jul 13, 2002* | Newport | ATP 250 | QF | Grass | James Blake | 5-7 5-7 | L | H2H | Match data |
| Jul 12, 2002* | Newport | ATP 250 | R16 | Grass | Jonathan Erlich | 6-4 6-0 | W | H2H | Match data |
| Jul 11, 2002* | Newport | ATP 250 | R32 | Grass | Ben Ellwood | 6-2 0-6 6-3 | W | H2H | Match data |
| Jun 25, 2002* | Wimbledon | Grand Slam | Q3 | Grass | Nicolas Thomann | 4-6 6-4 7-5 3-6 12-14 | L | H2H | Match data |
| Jun 25, 2002* | Wimbledon | Grand Slam | Q2 | Grass | Artem Derepasko | 7-5 6-3 | W | H2H | Match data |
| Jun 24, 2002 | Wimbledon | Grand Slam | Q1 | Grass | Jonathan Marray | 2-6 7-5 6-3 | W | H2H | Match data |
| Feb 28, 2002* | San Jose | ATP 250 | R32 | Hard | Davide Sanguinetti | 3-6 4-6 | L | H2H | Match data |
| Feb 22, 2002* | Memphis | ATP 250 | R16 | Hard | Tommy Haas | 6-7(7) 2-6 | L | H2H | Match data |
| Feb 21, 2002* | Memphis | ATP 250 | R32 | Hard | Mardy Fish | 6-3 7-6(4) | W | H2H | Match data |
| Jan 15, 2002* | Australian Open | Grand Slam | Q2 | Hard | Nicolas Coutelot | 3-6 3-6 | L | H2H | Match data |
| Jan 14, 2002 | Australian Open | Grand Slam | Q1 | Hard | Konstantinos Economidis | 6-2 6-2 | W | H2H | Match data |
| Sep 21, 2001* | Shanghai | ATP 250 | R16 | Hard | Irakli Labadze | 7-6(2) 6-7(3) 2-6 | L | H2H | Match data |
| Sep 20, 2001* | Shanghai | ATP 250 | R32 | Hard | Paradorn Srichaphan | 7-6(6) 3-6 6-4 | W | H2H | Match data |
| Aug 31, 2001* | US Open | Grand Slam | R64 | Hard | Goran Ivanisevic | 3-6 3-6 3-6 | L | H2H | Match data |
| Aug 29, 2001* | US Open | Grand Slam | R128 | Hard | Michal Tabara | 6-4 3-6 4-6 6-4 6-2 | W | H2H | Match data |
| Aug 28, 2001* | US Open | Grand Slam | Q3 | Hard | Jeff Morrison | 6-4 6-4 | W | H2H | Match data |
| Aug 28, 2001* | US Open | Grand Slam | Q2 | Hard | Nicolas Thomann | 1-6 6-3 6-4 | W | H2H | Match data |
| Aug 27, 2001 | US Open | Grand Slam | Q1 | Hard | Ytai Abougzir | 6-0 6-2 | W | H2H | Match data |
| Aug 15, 2001* | Washington | ATP 250 | R64 | Hard | Cecil Mamiit | 3-6 2-6 | L | H2H | Match data |
| Jul 26, 2001* | Los Angeles | ATP 250 | R32 | Hard | Xavier Malisse | 4-6 5-7 | L | H2H | Match data |
| Jul 12, 2001* | Newport | ATP 250 | R32 | Grass | Kristian Capalik | 2-6 5-7 | L | H2H | Match data |
| Jun 14, 2001* | Queen's Club | ATP 250 | R32 | Grass | Jan-Michael Gambill | 3-6 5-7 | L | H2H | Match data |
| Jun 13, 2001* | Queen's Club | ATP 250 | R64 | Grass | Cecil Mamiit | 6-1 7-6(5) | W | H2H | Match data |
| Mar 20, 2001* | Miami Masters | Masters 1000 | R128 | Hard | Andreas Vinciguerra | 6-3 2-6 0-6 | L | H2H | Match data |
| Mar 1, 2001* | San Jose | ATP 250 | R32 | Hard | Sargis Sargsian | 1-6 6-7(5) | L | H2H | Match data |
| Feb 21, 2001* | Memphis | ATP 250 | R64 | Hard | George Bastl | 6-1 6-7(4) 2-6 | L | H2H | Match data |
| Feb 15, 2001* | Marseille | ATP 250 | R32 | Hard | Jean-Rene Lisnard | 6-7(5) 2-6 | L | H2H | Match data |
| Jan 17, 2001* | Australian Open | Grand Slam | R128 | Hard | Christophe Rochus | 6-4 6-3 4-6 0-6 7-9 | L | H2H | Match data |
| Jan 4, 2001* | Adelaide | ATP 250 | R32 | Hard | Andrei Pavel | 2-6 2-6 | L | H2H | Match data |
| Sep 16, 2000* | Tashkent | ATP 250 | QF | Hard | Davide Sanguinetti | 0-6 7-5 3-6 | L | H2H | Match data |
| Sep 15, 2000* | Tashkent | ATP 250 | R16 | Hard | Harel Levy | 6-4 6-3 | W | H2H | Match data |
| Sep 14, 2000* | Tashkent | ATP 250 | R32 | Hard | Jan Siemerink | 6-4 6-3 | W | H2H | Match data |
| Sep 1, 2000* | US Open | Grand Slam | R64 | Hard | Pete Sampras | 3-6 1-6 3-6 | L | H2H | Match data |
| Aug 30, 2000* | US Open | Grand Slam | R128 | Hard | Christophe Rochus | 3-6 6-3 6-4 7-6(4) | W | H2H | Match data |
| Aug 23, 2000* | Long Island | ATP 250 | R64 | Hard | Andrei Pavel | 4-6 1-6 | L | H2H | Match data |
| Jul 29, 2000* | Los Angeles | ATP 250 | SF | Hard | Michael Chang | 6-3 3-6 0-6 | L | H2H | Match data |
| Jul 29, 2000* | Los Angeles | ATP 250 | QF | Hard | Paul Goldstein | 3-0 (ret.) | W | H2H | Match data |
| Jul 28, 2000* | Los Angeles | ATP 250 | R16 | Hard | Mark Philippoussis | 3-6 7-6(5) 7-6(3) | W | H2H | Match data |
| Jul 27, 2000* | Los Angeles | ATP 250 | R32 | Hard | James Sekulov | 6-3 6-3 | W | H2H | Match data |
| Jul 13, 2000* | Newport | ATP 250 | R32 | Grass | Tuomas Ketola | 6-7(4) 6-2 3-6 | L | H2H | Match data |
| Jul 2, 2000* | Wimbledon | Grand Slam | R32 | Grass | Pete Sampras | 6-2 4-6 2-6 2-6 | L | H2H | Match data |
| Jun 30, 2000* | Wimbledon | Grand Slam | R64 | Grass | Michael Llodra | 7-6(3) 6-3 6-4 | W | H2H | Match data |
| Jun 28, 2000* | Wimbledon | Grand Slam | R128 | Grass | Barry Cowan | 6-3 6-4 6-7(5) 6-3 | W | H2H | Match data |
| Jun 22, 2000* | Nottingham | ATP 250 | R32 | Grass | Wayne Ferreira | 5-7 7-6(6) 3-6 | L | H2H | Match data |
| Jun 16, 2000* | Queen's Club | ATP 250 | R16 | Grass | Cedric Pioline | 4-6 5-7 | L | H2H | Match data |
| Jun 15, 2000* | Queen's Club | ATP 250 | R32 | Grass | Fabrice Santoro | 4-6 6-4 6-0 | W | H2H | Match data |
| Jun 14, 2000* | Queen's Club | ATP 250 | R64 | Grass | Vincent Spadea | 2-6 6-4 6-1 | W | H2H | Match data |
| May 31, 2000* | Roland Garros | Grand Slam | R128 | Clay | Michel Kratochvil | 4-6 7-6(3) 3-6 1-6 | L | H2H | Match data |
| May 4, 2000* | Orlando | ATP 250 | R32 | Clay | Jan Siemerink | 6-4 2-6 5-7 | L | H2H | Match data |
| Apr 13, 2000* | Atlanta | ATP 250 | R32 | Clay | Jiri Vanek | 5-7 4-6 | L | H2H | Match data |
| Mar 21, 2000* | Miami Masters | Masters 1000 | R128 | Hard | Roger Federer | 5-7 3-6 | L | H2H | Match data |
| Mar 15, 2000* | Indian Wells Masters | Masters 1000 | R64 | Hard | Gustavo Kuerten | 5-7 6-3 3-6 | L | H2H | Match data |
| Mar 4, 2000* | Delray Beach | ATP 250 | QF | Hard | Richard Fromberg | 6-4 6-7(3) 2-6 | L | H2H | Match data |
| Mar 3, 2000* | Delray Beach | ATP 250 | R16 | Hard | Cecil Mamiit | 1-6 7-6(3) 6-4 | W | H2H | Match data |
| Mar 2, 2000* | Delray Beach | ATP 250 | R32 | Hard | Karim Alami | 6-4 2-6 7-6(2) | W | H2H | Match data |
| Feb 16, 2000* | Memphis | ATP 250 | R64 | Hard | Martin Rodriguez | 6-7(4) 6-7(3) | L | H2H | Match data |
| Feb 12, 2000* | San Jose | ATP 250 | QF | Hard | Mark Philippoussis | 6-7(5) 4-6 | L | H2H | Match data |
| Feb 11, 2000* | San Jose | ATP 250 | R16 | Hard | Tomas Zib | 6-4 7-6(4) | W | H2H | Match data |
| Feb 10, 2000* | San Jose | ATP 250 | R32 | Hard | Jan-Michael Gambill | 7-6(2) 6-2 | W | H2H | Match data |
| Nov 12, 1999* | Moscow | ATP 250 | R16 | Carpet | Fabrice Santoro | 7-5 1-6 6-7(6) | L | H2H | Match data |
| Nov 11, 1999* | Moscow | ATP 250 | R32 | Carpet | Andrei Cherkasov | 6-3 6-3 | W | H2H | Match data |
| Oct 27, 1999* | Stuttgart Masters | Masters 1000 | R64 | Hard | Wayne Ferreira | 4-6 6-4 4-6 | L | H2H | Match data |
| Oct 14, 1999* | Singapore | ATP 250 | R32 | Hard | Jan-Michael Gambill | 6-7(2) 4-6 | L | H2H | Match data |
| Oct 7, 1999* | Shanghai | ATP 250 | R32 | Hard | Ivan Ljubicic | 6-7(1) 3-6 | L | H2H | Match data |
| Sep 5, 1999* | US Open | Grand Slam | R32 | Hard | Andre Agassi | 1-6 6-4 3-6 4-6 | L | H2H | Match data |
| Sep 3, 1999* | US Open | Grand Slam | R64 | Hard | Daniel Vacek | 6-2 3-6 2-6 6-4 6-3 | W | H2H | Match data |
| Sep 1, 1999* | US Open | Grand Slam | R128 | Hard | Andrea Gaudenzi | 6-1 6-3 6-2 | W | H2H | Match data |
| Aug 20, 1999* | Washington | ATP 250 | R16 | Hard | Yevgeny Kafelnikov | 5-7 4-6 | L | H2H | Match data |
| Aug 19, 1999* | Washington | ATP 250 | R32 | Hard | Wayne Arthurs | 6-4 6-1 | W | H2H | Match data |
| Aug 18, 1999* | Washington | ATP 250 | R64 | Hard | Richard Fromberg | 6-4 2-6 7-6(4) | W | H2H | Match data |
| Aug 14, 1999* | Cincinnati Masters | Masters 1000 | R16 | Hard | Richard Krajicek | 4-6 2-6 | L | H2H | Match data |
| Aug 12, 1999* | Cincinnati Masters | Masters 1000 | R32 | Hard | Todd Martin | 6-4 6-4 | W | H2H | Match data |
| Aug 11, 1999* | Cincinnati Masters | Masters 1000 | R64 | Hard | Jason Stoltenberg | 6-2 6-3 | W | H2H | Match data |
| Aug 4, 1999* | Canada Masters | Masters 1000 | R64 | Hard | Sebastien Lareau | 6-7(2) 1-6 | L | H2H | Match data |
| Jul 30, 1999* | Los Angeles | ATP 250 | R16 | Hard | Wayne Ferreira | 7-5 5-7 2-6 | L | H2H | Match data |
| Jul 29, 1999* | Los Angeles | ATP 250 | R32 | Hard | Taylor Dent | 6-2 6-2 | W | H2H | Match data |
| Jul 8, 1999* | Newport | ATP 250 | R32 | Grass | Max Mirnyi | 3-6 6-7(2) | L | H2H | Match data |
| Jun 23, 1999* | Wimbledon | Grand Slam | R128 | Grass | Jens Knippschild | 3-6 6-2 7-5 2-6 7-9 | L | H2H | Match data |
| Jun 17, 1999* | Nottingham | ATP 250 | R32 | Grass | Jerome Golmard | 4-6 7-6(5) 6-7(5) | L | H2H | Match data |
| Jun 11, 1999* | Halle | ATP 250 | R16 | Grass | Nicklas Kulti | 4-6 4-6 | L | H2H | Match data |
| Jun 10, 1999* | Halle | ATP 250 | R32 | Grass | Jonathan Stark | 6-3 6-4 | W | H2H | Match data |
| May 26, 1999* | Roland Garros | Grand Slam | R128 | Clay | Fernando Meligeni | 3-6 3-6 3-6 | L | H2H | Match data |
| May 20, 1999* | St. Poelten | ATP 250 | R32 | Clay | Mariano Zabaleta | 4-6 5-7 | L | H2H | Match data |
| May 7, 1999* | Delray Beach | ATP 250 | R16 | Clay | Hernan Gumy | 6-7(2) 6-7(2) | L | H2H | Match data |
| May 6, 1999* | Delray Beach | ATP 250 | R32 | Clay | Petr Korda | 6-4 6-2 | W | H2H | Match data |
| Apr 30, 1999* | Atlanta | ATP 250 | R16 | Clay | Jim Courier | 1-6 6-7(5) | L | H2H | Match data |
| Apr 29, 1999* | Atlanta | ATP 250 | R32 | Clay | Jan-Michael Gambill | 6-0 6-4 | W | H2H | Match data |
| Apr 22, 1999* | Orlando | ATP 250 | R32 | Clay | Jason Stoltenberg | 0-6 7-6(5) 4-6 | L | H2H | Match data |
| Mar 16, 1999* | Miami Masters | Masters 1000 | R128 | Hard | Andrei Medvedev | 1-6 0-6 | L | H2H | Match data |