Match log updated: 2026-08-30 18:41 UTC
Jan-Michael Gambill — ATP Match Log
Main draw matches: 392 | W: 201 | L: 191 | Win %: 51.3%
| Opponent | Score | Result | H2H | Match Data | Date ↓ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| Christian Ruud | 5-7 6-3 2-6 | L | H2H | Match data | May 3, 2001* | R32 | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Andre Agassi | 6-7(4) 1-6 0-6 | L | H2H | Match data | Mar 26, 2001* | F | Miami Open | Masters 1000 | Hard |
| Lleyton Hewitt | 7-5 6-4 | W | H2H | Match data | Mar 25, 2001* | SF | Miami Open | Masters 1000 | Hard |
| Gaston Gaudio | 3-6 7-5 6-4 | W | H2H | Match data | Mar 25, 2001* | QF | Miami Open | Masters 1000 | Hard |
| Jonas Bjorkman | 6-1 6-2 | W | H2H | Match data | Mar 24, 2001* | R16 | Miami Open | Masters 1000 | Hard |
| Thomas Enqvist | 7-5 6-7(7) 6-1 | W | H2H | Match data | Mar 22, 2001* | R32 | Miami Open | Masters 1000 | Hard |
| Andrew Ilie | 6-7(7) 7-6(6) 6-3 | W | H2H | Match data | Mar 21, 2001* | R64 | Miami Open | Masters 1000 | Hard |
| Yevgeny Kafelnikov | 4-6 3-6 | L | H2H | Match data | Mar 18, 2001* | QF | Indian Wells Open | Masters 1000 | Hard |
| Gustavo Kuerten | 7-6(5) 6-4 | W | H2H | Match data | Mar 17, 2001* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Fernando Vicente | 6-3 6-2 | W | H2H | Match data | Mar 15, 2001* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Dominik Hrbaty | 6-4 6-3 | W | H2H | Match data | Mar 14, 2001* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Xavier Malisse | 7-5 6-4 | W | H2H | Match data | Mar 11, 2001* | F | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Wayne Arthurs | 6-3 6-7(3) 7-6(8) | W | H2H | Match data | Mar 10, 2001* | SF | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Chris Woodruff | 5-7 7-6(9) 6-4 | W | H2H | Match data | Mar 10, 2001* | QF | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Greg Rusedski | (w/o) | W | H2H | Match data | Mar 9, 2001* | R16 | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Sergi Bruguera | 6-3 6-4 | W | H2H | Match data | Mar 8, 2001* | R32 | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Andre Agassi | 4-6 4-6 | L | H2H | Match data | Mar 3, 2001* | SF | San Jose | ATP International Series → modern equivalent ATP 250 | Hard |
| Juan Balcells | 6-2 6-0 | W | H2H | Match data | Mar 3, 2001* | QF | San Jose | ATP International Series → modern equivalent ATP 250 | Hard |
| Andy Roddick | 7-6(5) 7-6(1) | W | H2H | Match data | Mar 2, 2001* | R16 | San Jose | ATP International Series → modern equivalent ATP 250 | Hard |
| Andre Sa | 6-3 6-7(0) 6-3 | W | H2H | Match data | Mar 1, 2001* | R32 | San Jose | ATP International Series → modern equivalent ATP 250 | Hard |
| Tommy Haas | 4-6 2-6 | L | H2H | Match data | Feb 24, 2001* | QF | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Juan Balcells | 6-0 7-5 | W | H2H | Match data | Feb 23, 2001* | R16 | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Xavier Malisse | 7-6(2) 6-3 | W | H2H | Match data | Feb 22, 2001* | R32 | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Julien Boutter | 4-6 4-6 | L | H2H | Match data | Feb 3, 2001* | QF | Milan | ATP International Series → modern equivalent ATP 250 | Carpet |
| Sergi Bruguera | 6-3 7-5 | W | H2H | Match data | Feb 2, 2001* | R16 | Milan | ATP International Series → modern equivalent ATP 250 | Carpet |
| Sjeng Schalken | 6-1 6-7(3) 6-2 | W | H2H | Match data | Feb 1, 2001* | R32 | Milan | ATP International Series → modern equivalent ATP 250 | Carpet |
| Chris Woodruff | 3-6 6-4 6-4 5-7 3-6 | L | H2H | Match data | Jan 17, 2001* | R128 | Australian Open | Grand Slam | Hard |
| Francisco Clavet | 4-6 4-6 | L | H2H | Match data | Jan 13, 2001* | QF | ASB Classic | ATP International Series → modern equivalent ATP 250 | Hard |
| Andreas Vinciguerra | 6-4 6-4 | W | H2H | Match data | Jan 12, 2001* | R16 | ASB Classic | ATP International Series → modern equivalent ATP 250 | Hard |
| Nicolas Massu | 7-6(4) 6-4 | W | H2H | Match data | Jan 11, 2001* | R32 | ASB Classic | ATP International Series → modern equivalent ATP 250 | Hard |
| Magnus Norman | (w/o) | L | H2H | Match data | Nov 24, 2000* | R16 | Stockholm Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Max Mirnyi | 7-5 6-3 | W | H2H | Match data | Nov 23, 2000* | R32 | Stockholm Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Juan Carlos Ferrero | 6-4 5-7 4-6 | L | H2H | Match data | Nov 18, 2000* | R16 | Paris Masters | Masters 1000 | Carpet |
| Stephane Huet | 6-3 7-5 | W | H2H | Match data | Nov 16, 2000* | R32 | Paris Masters | Masters 1000 | Carpet |
| Andrei Pavel | 4-1 (ret.) | W | H2H | Match data | Nov 15, 2000* | R64 | Paris Masters | Masters 1000 | Carpet |
| Roger Federer | 6-7(3) 0-1 (ret.) | L | H2H | Match data | Nov 1, 2000* | R64 | Stuttgart Masters | Masters 1000 | Hard |
| Thomas Enqvist | 6-7(14) 6-7(5) | L | H2H | Match data | Oct 26, 2000* | R32 | Swiss Indoors | ATP International Series → modern equivalent ATP 250 | Carpet |
| Carlos Moya | 7-6(4) 6-7(10) 4-6 | L | H2H | Match data | Oct 21, 2000* | QF | Toulouse | ATP International Series → modern equivalent ATP 250 | Hard |
| Hicham Arazi | 6-3 7-5 | W | H2H | Match data | Oct 20, 2000* | R16 | Toulouse | ATP International Series → modern equivalent ATP 250 | Hard |
| Francisco Clavet | 6-7(7) 7-6(6) 6-3 | W | H2H | Match data | Oct 19, 2000* | R32 | Toulouse | ATP International Series → modern equivalent ATP 250 | Hard |
| Arnaud Clement | 4-6 0-6 | L | H2H | Match data | Oct 12, 2000* | R32 | Vienna Open | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Thomas Johansson | 6-3 3-6 6-7(5) 6-7(1) | L | H2H | Match data | Sep 3, 2000* | R32 | US Open | Grand Slam | Hard |
| Mark Philippoussis | 6-4 6-4 6-4 | W | H2H | Match data | Sep 1, 2000* | R64 | US Open | Grand Slam | Hard |
| Mardy Fish | 5-7 5-7 6-4 6-3 6-2 | W | H2H | Match data | Aug 30, 2000* | R128 | US Open | Grand Slam | Hard |
| Carlos Moya | 6-3 6-7(2) 6-7(5) | L | H2H | Match data | Aug 25, 2000* | R16 | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Thomas Johansson | 7-6(5) 7-5 | W | H2H | Match data | Aug 24, 2000* | R32 | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Nicolas Kiefer | 6-4 4-6 2-6 | L | H2H | Match data | Aug 19, 2000* | QF | Washington Open | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Christophe Rochus | 6-0 6-1 | W | H2H | Match data | Aug 18, 2000* | R16 | Washington Open | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Alex Obrien | 6-3 5-7 7-5 | W | — | Match data | Aug 17, 2000* | R32 | Washington Open | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Michael Chang | 7-6(2) 3-6 (ret.) | L | H2H | Match data | Jul 30, 2000* | F | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Arnaud Clement | 3-6 6-0 6-3 | W | H2H | Match data | Jul 29, 2000* | SF | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Jason Stoltenberg | 6-1 3-6 6-1 | W | H2H | Match data | Jul 29, 2000* | QF | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Laurence Tieleman | 7-6(2) 6-2 | W | H2H | Match data | Jul 28, 2000* | R16 | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Cecil Mamiit | 6-3 6-2 | W | H2H | Match data | Jul 27, 2000* | R32 | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Pete Sampras | 4-6 7-6(4) 4-6 4-6 | L | H2H | Match data | Jul 7, 2000* | QF | Wimbledon | Grand Slam | Grass |
| Thomas Enqvist | 7-6(5) 3-6 6-3 6-4 | W | H2H | Match data | Jul 5, 2000* | R16 | Wimbledon | Grand Slam | Grass |
| Paul Goldstein | 7-6(10) 6-2 6-2 | W | H2H | Match data | Jul 2, 2000* | R32 | Wimbledon | Grand Slam | Grass |
| Fabrice Santoro | 4-6 6-4 6-2 6-2 | W | H2H | Match data | Jun 30, 2000* | R64 | Wimbledon | Grand Slam | Grass |
| Lleyton Hewitt | 6-3 6-2 7-5 | W | H2H | Match data | Jun 28, 2000* | R128 | Wimbledon | Grand Slam | Grass |
| Byron Black | 6-7(5) 1-6 | L | H2H | Match data | Jun 24, 2000* | SF | Eastbourne Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Gianluca Pozzi | 6-4 6-4 | W | H2H | Match data | Jun 24, 2000* | QF | Eastbourne Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Fabrice Santoro | 7-6(0) 6-1 | W | H2H | Match data | Jun 23, 2000* | R16 | Eastbourne Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Martin Lee | 6-3 6-3 | W | H2H | Match data | Jun 22, 2000* | R32 | Eastbourne Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Cedric Pioline | 7-5 2-6 3-6 | L | H2H | Match data | Jun 15, 2000* | R32 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Adrian Voinea | 6-3 6-3 | W | H2H | Match data | Jun 14, 2000* | R64 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Roger Federer | 6-7(5) 3-6 3-6 | L | H2H | Match data | Jun 2, 2000* | R64 | Roland Garros | Grand Slam | Clay |
| Nicolas Kiefer | 6-3 7-5 6-1 | W | H2H | Match data | May 31, 2000* | R128 | Roland Garros | Grand Slam | Clay |
| Andrei Pavel | 3-6 5-7 | L | H2H | Match data | May 26, 2000* | R16 | St. Poelten | ATP International Series → modern equivalent ATP 250 | Clay |
| Ivan Ljubicic | 7-5 6-1 | W | H2H | Match data | May 25, 2000* | R32 | St. Poelten | ATP International Series → modern equivalent ATP 250 | Clay |
| Andrei Medvedev | 6-1 5-7 2-6 | L | H2H | Match data | May 18, 2000* | R32 | Hamburg Open | Masters 1000 | Clay |
| Michael Chang | 7-5 7-5 | W | H2H | Match data | May 17, 2000* | R64 | Hamburg Open | Masters 1000 | Clay |
| Ramon Delgado | 7-5 5-7 4-6 | L | H2H | Match data | May 4, 2000* | R32 | Orlando | ATP International Series → modern equivalent ATP 250 | Clay |
| Lleyton Hewitt | 4-6 6-7(3) | L | H2H | Match data | Mar 26, 2000* | QF | Miami Open | Masters 1000 | Hard |
| Mark Philippoussis | 6-2 6-7(6) 6-3 | W | H2H | Match data | Mar 25, 2000* | R16 | Miami Open | Masters 1000 | Hard |
| Magnus Norman | 6-3 3-6 6-3 | W | H2H | Match data | Mar 23, 2000* | R32 | Miami Open | Masters 1000 | Hard |
| Karim Alami | 6-4 5-7 6-1 | W | H2H | Match data | Mar 22, 2000* | R64 | Miami Open | Masters 1000 | Hard |
| Slava Dosedel | 6-4 6-1 | W | H2H | Match data | Mar 21, 2000* | R128 | Miami Open | Masters 1000 | Hard |
| Wayne Ferreira | 4-6 7-6(12) 4-6 | L | H2H | Match data | Mar 15, 2000* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Stefan Koubek | 1-6 6-7(7) | L | H2H | Match data | Mar 3, 2000* | R16 | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Julian Alonso | 6-4 3-0 (ret.) | W | H2H | Match data | Mar 2, 2000* | R32 | Delray Beach Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Hicham Arazi | 4-6 5-7 | L | H2H | Match data | Feb 24, 2000* | R32 | London | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Rainer Schuettler | 2-6 6-1 6-7(2) | L | H2H | Match data | Feb 18, 2000* | R16 | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Orlin Stanoytchev | 6-2 6-3 | W | H2H | Match data | Feb 17, 2000* | R32 | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Justin Gimelstob | 6-7(2) 2-6 | L | H2H | Match data | Feb 10, 2000* | R32 | San Jose | ATP International Series → modern equivalent ATP 250 | Hard |
| Wayne Black | 6-7(3) 1-6 4-6 | L | H2H | Match data | Jan 19, 2000* | R128 | Australian Open | Grand Slam | Hard |
| Magnus Norman | 3-6 3-6 | L | H2H | Match data | Jan 14, 2000* | R16 | ASB Classic | ATP International Series → modern equivalent ATP 250 | Hard |
| Richard Fromberg | 4-6 6-3 6-4 | W | H2H | Match data | Jan 13, 2000* | R32 | ASB Classic | ATP International Series → modern equivalent ATP 250 | Hard |
| Sebastien Grosjean | 6-3 6-7(4) 2-6 | L | H2H | Match data | Jan 7, 2000* | R16 | Adelaide International | ATP International Series → modern equivalent ATP 250 | Hard |
| Wayne Arthurs | 3-6 7-6(5) 6-4 | W | H2H | Match data | Jan 6, 2000* | R32 | Adelaide International | ATP International Series → modern equivalent ATP 250 | Hard |
| Magnus Gustafsson | 0-6 6-2 6-7(4) | L | H2H | Match data | Nov 13, 1999* | SF | Stockholm Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Mark Philippoussis | 4-6 6-2 7-5 | W | H2H | Match data | Nov 13, 1999* | QF | Stockholm Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Tim Henman | 7-5 6-3 | W | H2H | Match data | Nov 12, 1999* | R16 | Stockholm Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Arnaud Di Pasquale | 6-2 6-3 | W | H2H | Match data | Nov 11, 1999* | R32 | Stockholm Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Sebastien Grosjean | 6-1 3-6 3-6 | L | H2H | Match data | Oct 21, 1999* | R32 | Montpellier Open | ATP World Series → modern equivalent ATP 250 | Carpet |
| Jan Kroslak | 6-1 6-2 | W | H2H | Match data | Oct 20, 1999* | R64 | Montpellier Open | ATP World Series → modern equivalent ATP 250 | Carpet |
| Marcelo Rios | 4-6 4-6 | L | H2H | Match data | Oct 16, 1999* | QF | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Michael Chang | 6-2 7-6(4) | W | H2H | Match data | Oct 15, 1999* | R16 | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Justin Gimelstob | 7-6(2) 6-4 | W | H2H | Match data | Oct 14, 1999* | R32 | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Michael Chang | 3-6 5-7 | L | H2H | Match data | Oct 9, 1999* | QF | Shanghai Masters | ATP World Series → modern equivalent ATP 250 | Hard |
| Antony Dupuis | 6-3 6-4 | W | H2H | Match data | Oct 8, 1999* | R16 | Shanghai Masters | ATP World Series → modern equivalent ATP 250 | Hard |
| Yu Jr. Wang | 6-0 6-1 | W | H2H | Match data | Oct 7, 1999* | R32 | Shanghai Masters | ATP World Series → modern equivalent ATP 250 | Hard |
| Fabrice Santoro | 4-6 2-6 6-3 7-6(7) 4-4 (ret.) | L | H2H | Match data | Sep 3, 1999* | R64 | US Open | Grand Slam | Hard |
| Stefan Koubek | 7-5 6-1 6-4 | W | H2H | Match data | Sep 1, 1999* | R128 | US Open | Grand Slam | Hard |
| Richard Krajicek | 4-6 3-6 | L | H2H | Match data | Aug 26, 1999* | R32 | Long Island | ATP World Series → modern equivalent ATP 250 | Hard |
| Kenneth Carlsen | 6-7(3) 6-4 4-6 | L | H2H | Match data | Aug 18, 1999* | R64 | Washington Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Nicolas Lapentti | 0-6 6-7(3) | L | H2H | Match data | Aug 12, 1999* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Sjeng Schalken | 4-6 6-3 6-4 | W | H2H | Match data | Aug 11, 1999* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Wayne Ferreira | 5-7 6-3 6-7(8) | L | H2H | Match data | Aug 5, 1999* | R32 | Canadian Open | Masters 1000 | Hard |
| Jocelyn Robichaud | 6-0 6-0 | W | H2H | Match data | Aug 4, 1999* | R64 | Canadian Open | Masters 1000 | Hard |
| Andre Agassi | 2-6 2-6 | L | H2H | Match data | Jul 29, 1999* | R32 | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Lorenzo Manta | 4-6 4-6 6-3 7-6(4) 3-6 | L | H2H | Match data | Jun 25, 1999* | R64 | Wimbledon | Grand Slam | Grass |
| Franco Squillari | 6-1 6-3 7-6(5) | W | H2H | Match data | Jun 23, 1999* | R128 | Wimbledon | Grand Slam | Grass |
| Greg Rusedski | 6-4 4-6 5-7 | L | H2H | Match data | Jun 18, 1999* | R16 | Eastbourne Open | ATP World Series → modern equivalent ATP 250 | Grass |
| Chris Woodruff | 7-6(1) 6-4 | W | H2H | Match data | Jun 17, 1999* | R32 | Eastbourne Open | ATP World Series → modern equivalent ATP 250 | Grass |
| Mark Philippoussis | 6-2 3-6 4-6 | L | H2H | Match data | Jun 10, 1999* | R32 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Michael Sell | 6-4 6-2 | W | H2H | Match data | Jun 9, 1999* | R64 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Richard Krajicek | 6-7(4) 3-6 2-6 | L | H2H | Match data | May 26, 1999* | R128 | Roland Garros | Grand Slam | Clay |
| Richard Krajicek | 0-6 6-3 1-6 | L | H2H | Match data | May 12, 1999* | R64 | Italian Open | Masters 1000 | Clay |
| Gustavo Kuerten | 4-6 4-6 | L | H2H | Match data | May 6, 1999* | R32 | Hamburg Open | Masters 1000 | Clay |
| Fredrik Jonsson | 3-6 6-2 6-3 | W | H2H | Match data | May 5, 1999* | R64 | Hamburg Open | Masters 1000 | Clay |
| Justin Gimelstob | 0-6 4-6 | L | H2H | Match data | Apr 29, 1999* | R32 | Atlanta | ATP World Series → modern equivalent ATP 250 | Clay |
| Sargis Sargsian | 6-3 3-6 6-7(4) | L | H2H | Match data | Apr 22, 1999* | R32 | Orlando | ATP World Series → modern equivalent ATP 250 | Clay |
| Fabrice Santoro | 5-7 2-6 | L | H2H | Match data | Mar 17, 1999* | R64 | Miami Open | Masters 1000 | Hard |
| Xavier Malisse | 7-5 6-2 | W | H2H | Match data | Mar 16, 1999* | R128 | Miami Open | Masters 1000 | Hard |
| Richard Krajicek | 7-6(3) 5-7 5-7 | L | H2H | Match data | Mar 11, 1999* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Jiri Novak | 6-2 7-6(3) | W | H2H | Match data | Mar 10, 1999* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Lleyton Hewitt | 7-6(2) 4-6 6-4 | W | H2H | Match data | Mar 7, 1999* | F | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Andre Agassi | 5-4 (ret.) | W | H2H | Match data | Mar 6, 1999* | SF | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Justin Gimelstob | 4-6 6-4 6-1 | W | H2H | Match data | Mar 6, 1999* | QF | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Pete Sampras | 4-6 6-3 6-4 | W | H2H | Match data | Mar 5, 1999* | R16 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Franco Squillari | 3-6 6-3 6-4 | W | H2H | Match data | Mar 4, 1999* | R32 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Davide Sanguinetti | 4-6 4-6 | L | H2H | Match data | Feb 25, 1999* | R32 | London | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Todd Martin | 6-3 5-7 6-7(7) | L | H2H | Match data | Feb 20, 1999* | QF | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Scott Draper | 6-3 7-6(6) | W | H2H | Match data | Feb 19, 1999* | R16 | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Alex Calatrava | 6-4 6-2 | W | H2H | Match data | Feb 18, 1999* | R32 | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Justin Gimelstob | 3-6 6-7(6) | L | H2H | Match data | Feb 11, 1999* | R32 | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Thomas Enqvist | 3-6 6-7(5) 4-6 | L | H2H | Match data | Jan 20, 1999* | R128 | Australian Open | Grand Slam | Hard |
| Albert Costa | 3-6 5-7 | L | H2H | Match data | Jan 15, 1999* | R16 | Sydney International | ATP World Series → modern equivalent ATP 250 | Hard |
| Sandon Stolle | 7-6(7) 2-6 6-1 | W | H2H | Match data | Jan 14, 1999* | R32 | Sydney International | ATP World Series → modern equivalent ATP 250 | Hard |
| Pete Sampras | 1-4 (ret.) | L | H2H | Match data | Nov 1, 1998* | QF | Stuttgart Masters | Masters 1000 | Hard |
| Tim Henman | 7-6(2) 1-6 7-6(5) | W | H2H | Match data | Oct 31, 1998* | R16 | Stuttgart Masters | Masters 1000 | Hard |
| Alex Corretja | 6-2 6-4 | W | H2H | Match data | Oct 29, 1998* | R32 | Stuttgart Masters | Masters 1000 | Hard |
| Daniel Vacek | 6-3 4-6 6-3 | W | H2H | Match data | Oct 28, 1998* | R64 | Stuttgart Masters | Masters 1000 | Hard |
| Nicklas Kulti | 6-3 3-6 2-6 | L | H2H | Match data | Oct 22, 1998* | R32 | Ostrava | ATP World Series → modern equivalent ATP 250 | Carpet |
| Jim Courier | 4-6 4-6 | L | H2H | Match data | Oct 17, 1998* | QF | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Brett Steven | (w/o) | W | H2H | Match data | Oct 16, 1998* | R16 | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Jonathan Stark | 6-1 6-2 | W | H2H | Match data | Oct 15, 1998* | R32 | Brisbane International | ATP Championship Series → modern equivalent ATP 500 | Carpet |
| Michael Tebbutt | 0-5 (ret.) | L | H2H | Match data | Oct 9, 1998* | R16 | Shanghai Masters | ATP World Series → modern equivalent ATP 250 | Carpet |
| Yu Zhang | 6-4 6-3 | W | — | Match data | Oct 8, 1998* | R32 | Shanghai Masters | ATP World Series → modern equivalent ATP 250 | Carpet |
| Carlos Moya | 2-6 6-3 6-3 3-6 6-7(4) | L | H2H | Match data | Sep 6, 1998* | R32 | US Open | Grand Slam | Hard |
| Magnus Norman | 6-4 6-2 6-7(8) 6-3 | W | H2H | Match data | Sep 4, 1998* | R64 | US Open | Grand Slam | Hard |
| Karsten Braasch | 6-3 1-6 6-3 7-5 | W | H2H | Match data | Sep 2, 1998* | R128 | US Open | Grand Slam | Hard |
| Pete Sampras | 6-7(3) 3-6 | L | H2H | Match data | Aug 15, 1998* | R16 | Cincinnati Open | Masters 1000 | Hard |
| Cedric Pioline | 6-7(5) 7-6(5) 6-4 | W | H2H | Match data | Aug 13, 1998* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Olivier Delaitre | 6-1 6-3 | W | H2H | Match data | Aug 12, 1998* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Albert Costa | 4-6 2-6 | L | H2H | Match data | Aug 6, 1998* | R32 | Canadian Open | Masters 1000 | Hard |
| Nicolas Escude | 6-3 6-2 | W | H2H | Match data | Aug 5, 1998* | R64 | Canadian Open | Masters 1000 | Hard |
| Andre Agassi | 4-6 4-6 | L | H2H | Match data | Jul 31, 1998* | R16 | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Steve Campbell | 6-4 6-4 | W | H2H | Match data | Jul 30, 1998* | R32 | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Rainer Schuettler | 6-4 3-6 3-6 | L | H2H | Match data | Jul 22, 1998* | R64 | Washington Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Byron Black | 5-7 4-6 5-7 | L | H2H | Match data | Jun 26, 1998* | R64 | Wimbledon | Grand Slam | Grass |
| Sjeng Schalken | 7-6(6) 6-4 6-7(5) 4-6 8-6 | W | H2H | Match data | Jun 24, 1998* | R128 | Wimbledon | Grand Slam | Grass |
| Peter Wessels | 4-6 4-6 | L | H2H | Match data | Jun 18, 1998* | R32 | Libéma Open | ATP World Series → modern equivalent ATP 250 | Grass |
| Byron Black | 7-5 4-6 4-6 | L | H2H | Match data | Jun 11, 1998* | R32 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Lars Burgsmuller | 4-6 6-0 6-4 | W | H2H | Match data | Jun 10, 1998* | R64 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Daniel Vacek | 4-6 6-2 5-7 6-7(0) | L | H2H | Match data | May 29, 1998* | R64 | Roland Garros | Grand Slam | Clay |
| Martin Rodriguez | 6-3 6-2 6-4 | W | H2H | Match data | May 27, 1998* | R128 | Roland Garros | Grand Slam | Clay |
| Andrea Gaudenzi | 3-6 5-7 | L | H2H | Match data | May 21, 1998* | R32 | St. Poelten | ATP World Series → modern equivalent ATP 250 | Clay |
| Steve Campbell | 2-6 6-7(7) | L | H2H | Match data | May 1, 1998* | R16 | Atlanta | ATP World Series → modern equivalent ATP 250 | Clay |
| Mariano Zabaleta | 0-6 7-6(2) 7-5 | W | H2H | Match data | Apr 30, 1998* | R32 | Atlanta | ATP World Series → modern equivalent ATP 250 | Clay |
| Marcello Craca | 4-6 4-6 | L | H2H | Match data | Apr 24, 1998* | R16 | Orlando | ATP World Series → modern equivalent ATP 250 | Clay |
| Wayne Black | 7-6(5) 6-2 | W | H2H | Match data | Apr 23, 1998* | R32 | Orlando | ATP World Series → modern equivalent ATP 250 | Clay |
| Andrei Pavel | 4-6 3-6 | L | H2H | Match data | Apr 18, 1998* | SF | Japan Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Tim Henman | 6-3 4-6 6-3 | W | H2H | Match data | Apr 18, 1998* | QF | Japan Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Rainer Schuettler | 6-0 6-0 | W | H2H | Match data | Apr 17, 1998* | R16 | Japan Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Kotaro Miyachi | 6-0 6-3 | W | H2H | Match data | Apr 16, 1998* | R32 | Japan Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Stefano Pescosolido | 6-3 6-2 | W | H2H | Match data | Apr 15, 1998* | R64 | Japan Open | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Mark Woodforde | 1-6 2-6 | L | H2H | Match data | Mar 17, 1998* | R128 | Miami Open | Masters 1000 | Hard |
| Marcelo Rios | 6-7(3) 3-6 | L | H2H | Match data | Mar 15, 1998* | SF | Indian Wells Open | Masters 1000 | Hard |
| Andre Agassi | 7-6(6) 3-6 6-3 | W | H2H | Match data | Mar 15, 1998* | QF | Indian Wells Open | Masters 1000 | Hard |
| Jim Courier | 6-2 6-4 | W | H2H | Match data | Mar 14, 1998* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Francisco Clavet | 6-3 6-4 | W | H2H | Match data | Mar 12, 1998* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Mark Philippoussis | 7-6(7) 5-7 7-6(6) | W | H2H | Match data | Mar 11, 1998* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Andre Agassi | 3-6 6-7(5) | L | H2H | Match data | Mar 7, 1998* | QF | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Nicolas Kiefer | 6-2 6-1 | W | H2H | Match data | Mar 6, 1998* | R16 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Mark Woodforde | 6-4 2-6 7-5 | W | H2H | Match data | Mar 5, 1998* | R32 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Gustavo Kuerten | 4-6 6-7(4) | L | H2H | Match data | Feb 20, 1998* | R16 | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Byron Black | 5-7 7-5 7-6(7) | W | H2H | Match data | Feb 19, 1998* | R32 | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Sandon Stolle | 6-3 6-7(2) 6-4 | W | H2H | Match data | Feb 18, 1998* | R64 | Memphis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Andre Agassi | 5-7 6-7(7) | L | H2H | Match data | Feb 14, 1998* | QF | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Tomas Nydahl | 6-4 7-6(1) | W | H2H | Match data | Feb 13, 1998* | R16 | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Sargis Sargsian | 6-3 1-6 6-4 | W | H2H | Match data | Feb 12, 1998* | R32 | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Alex Obrien | 6-3 5-7 1-6 3-6 | L | — | Match data | Jan 21, 1998* | R128 | Australian Open | Grand Slam | Hard |
| Scott Draper | 4-6 3-6 6-7(11) | L | H2H | Match data | Aug 27, 1997* | R128 | US Open | Grand Slam | Hard |
| Petr Korda | 3-6 3-6 | L | H2H | Match data | Aug 14, 1997* | R32 | New Haven | Championship Series → modern equivalent ATP 500 | Hard |
| Filip Dewulf | 7-6(1) 7-5 | W | H2H | Match data | Aug 13, 1997* | R64 | New Haven | Championship Series → modern equivalent ATP 500 | Hard |
| Michael Chang | 3-6 3-6 | L | H2H | Match data | Apr 24, 1997* | R32 | Orlando | World Series → modern equivalent ATP 250 | Clay |
| Jacco Eltingh | 3-6 3-6 | L | H2H | Match data | Feb 19, 1997* | R64 | Memphis | Championship Series → modern equivalent ATP 500 | Hard |
| Jonas Bjorkman | 4-6 0-6 | L | H2H | Match data | Jan 11, 1997* | QF | ASB Classic | World Series → modern equivalent ATP 250 | Hard |
| Chris Woodruff | 5-7 6-2 7-6(2) | W | H2H | Match data | Jan 10, 1997* | R16 | ASB Classic | World Series → modern equivalent ATP 250 | Hard |
10 qualifying matches shown in the table; qualifying is excluded from main-draw summaries and leaderboards. Estimated from the tournament schedule where an exact match date is unavailable. Arrows show an edition's recorded category and documented modern equivalent; unresolved editions keep their recorded category. Mapping details.