Match log updated: 2026-08-31 13:51 UTC
Pete Sampras — ATP Match Log
Main draw matches: 948 | W: 739 | L: 209 | Win %: 78.0%
| Opponent | Score | Result | H2H | Match Data | Date ↓ | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|---|
| Andre Agassi | 6-3 6-4 5-7 6-4 | W | H2H | Match data | Sep 9, 2002* | F | US Open | Grand Slam | Hard |
| Sjeng Schalken | 7-6(6) 7-6(4) 6-2 | W | H2H | Match data | Sep 8, 2002* | SF | US Open | Grand Slam | Hard |
| Andy Roddick | 6-3 6-2 6-4 | W | H2H | Match data | Sep 6, 2002* | QF | US Open | Grand Slam | Hard |
| Tommy Haas | 7-5 6-4 6-7(5) 7-5 | W | H2H | Match data | Sep 4, 2002* | R16 | US Open | Grand Slam | Hard |
| Greg Rusedski | 7-6(4) 4-6 7-6(3) 3-6 6-4 | W | H2H | Match data | Sep 1, 2002* | R32 | US Open | Grand Slam | Hard |
| Kristian Pless | 6-3 7-5 6-4 | W | H2H | Match data | Aug 30, 2002* | R64 | US Open | Grand Slam | Hard |
| Albert Portas | 6-1 6-4 6-4 | W | H2H | Match data | Aug 28, 2002* | R128 | US Open | Grand Slam | Hard |
| Paul-Henri Mathieu | 3-6 7-6(7) 4-6 | L | H2H | Match data | Aug 22, 2002* | R32 | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Wayne Arthurs | 6-4 3-6 6-7(4) | L | H2H | Match data | Aug 8, 2002* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Guillermo Canas | 5-7 7-6(6) 6-3 | W | H2H | Match data | Aug 7, 2002* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Tommy Haas | 6-7(3) 6-3 6-7(5) | L | H2H | Match data | Aug 3, 2002* | R16 | Canadian Open | Masters 1000 | Hard |
| Hyung-Taik Lee | 3-6 7-6(5) 6-2 | W | H2H | Match data | Aug 1, 2002* | R32 | Canadian Open | Masters 1000 | Hard |
| Wayne Ferreira | 7-6(6) 5-7 6-4 | W | H2H | Match data | Jul 31, 2002* | R64 | Canadian Open | Masters 1000 | Hard |
| George Bastl | 3-6 2-6 6-4 6-3 4-6 | L | H2H | Match data | Jun 28, 2002* | R64 | Wimbledon | Grand Slam | Grass |
| Martin Lee | 6-3 7-6(1) 6-3 | W | H2H | Match data | Jun 26, 2002* | R128 | Wimbledon | Grand Slam | Grass |
| Nicolas Kiefer | 3-6 4-6 | L | H2H | Match data | Jun 14, 2002* | R16 | Halle Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Andrei Stoliarov | 4-6 6-3 6-4 | W | H2H | Match data | Jun 13, 2002* | R32 | Halle Open | ATP International Series → modern equivalent ATP 250 | Grass |
| Andrea Gaudenzi | 6-3 4-6 2-6 6-7(3) | L | H2H | Match data | May 29, 2002* | R128 | Roland Garros | Grand Slam | Clay |
| Max Mirnyi | 3-6 4-6 | L | H2H | Match data | May 15, 2002* | R64 | Hamburg Open | Masters 1000 | Clay |
| Felix Mantilla | 4-6 7-6(3) 3-6 | L | H2H | Match data | May 8, 2002* | R64 | Italian Open | Masters 1000 | Clay |
| Andy Roddick | 6-7(9) 3-6 | L | H2H | Match data | Apr 28, 2002* | F | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Andre Agassi | 6-1 7-5 | W | H2H | Match data | Apr 27, 2002* | SF | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Todd Martin | 6-2 7-6(3) | W | H2H | Match data | Apr 27, 2002* | QF | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Mariano Puerta | 6-4 6-2 | W | H2H | Match data | Apr 26, 2002* | R16 | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Jan Vacek | 4-6 6-1 7-5 | W | H2H | Match data | Apr 25, 2002* | R32 | U.S. Men's Clay Court Championship | ATP International Series → modern equivalent ATP 250 | Clay |
| Fernando Gonzalez | 6-7(1) 1-6 | L | H2H | Match data | Mar 21, 2002* | R32 | Miami Open | Masters 1000 | Hard |
| Jarkko Nieminen | 4-6 6-3 6-2 | W | H2H | Match data | Mar 20, 2002* | R64 | Miami Open | Masters 1000 | Hard |
| Lleyton Hewitt | 2-6 4-6 | L | H2H | Match data | Mar 17, 2002* | SF | Indian Wells Open | Masters 1000 | Hard |
| Rainer Schuettler | 6-2 6-4 | W | H2H | Match data | Mar 17, 2002* | QF | Indian Wells Open | Masters 1000 | Hard |
| Fabrice Santoro | 6-3 3-6 7-5 | W | H2H | Match data | Mar 16, 2002* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Albert Costa | 6-4 6-4 | W | H2H | Match data | Mar 14, 2002* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Mardy Fish | 7-6(5) 6-2 | W | H2H | Match data | Mar 13, 2002* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Wayne Ferreira | 5-7 5-7 | L | H2H | Match data | Mar 8, 2002* | R16 | Scottsdale | ATP International Series → modern equivalent ATP 250 | Hard |
| Byron Black | 6-1 6-2 | W | H2H | Match data | Mar 7, 2002* | R32 | Scottsdale | ATP International Series → modern equivalent ATP 250 | Hard |
| Marat Safin | 2-6 4-6 7-6(5) 6-7(8) | L | H2H | Match data | Jan 23, 2002* | R16 | Australian Open | Grand Slam | Hard |
| Nicolas Escude | 7-6(5) 5-7 6-4 6-7(6) 6-3 | W | H2H | Match data | Jan 20, 2002* | R32 | Australian Open | Grand Slam | Hard |
| Juan Ignacio Chela | 6-3 7-5 3-6 6-4 | W | H2H | Match data | Jan 18, 2002* | R64 | Australian Open | Grand Slam | Hard |
| Jarkko Nieminen | 6-3 6-3 6-4 | W | H2H | Match data | Jan 16, 2002* | R128 | Australian Open | Grand Slam | Hard |
| Todd Martin | 6-3 3-6 4-6 | L | H2H | Match data | Jan 3, 2002* | R32 | Adelaide International | ATP International Series → modern equivalent ATP 250 | Hard |
| Max Mirnyi | 4-6 2-6 | L | H2H | Match data | Oct 21, 2001* | QF | Stuttgart Masters | Masters 1000 | Hard |
| Marcelo Rios | 4-6 7-6(3) 6-4 | W | H2H | Match data | Oct 20, 2001* | R16 | Stuttgart Masters | Masters 1000 | Hard |
| Stefan Koubek | 6-3 7-6(5) | W | H2H | Match data | Oct 18, 2001* | R32 | Stuttgart Masters | Masters 1000 | Hard |
| Lleyton Hewitt | 6-7(4) 1-6 1-6 | L | H2H | Match data | Sep 10, 2001* | F | US Open | Grand Slam | Hard |
| Marat Safin | 6-3 7-6(5) 6-3 | W | H2H | Match data | Sep 9, 2001* | SF | US Open | Grand Slam | Hard |
| Andre Agassi | 6-7(7) 7-6(2) 7-6(2) 7-6(5) | W | H2H | Match data | Sep 7, 2001* | QF | US Open | Grand Slam | Hard |
| Patrick Rafter | 6-3 6-2 6-7(5) 6-4 | W | H2H | Match data | Sep 5, 2001* | R16 | US Open | Grand Slam | Hard |
| Mikhail Youzhny | 6-3 6-2 6-2 | W | H2H | Match data | Sep 2, 2001* | R32 | US Open | Grand Slam | Hard |
| Andre Sa | 7-6(4) 6-4 6-3 | W | H2H | Match data | Aug 31, 2001* | R64 | US Open | Grand Slam | Hard |
| Julien Boutter | 6-4 7-6(4) 7-6(6) | W | H2H | Match data | Aug 29, 2001* | R128 | US Open | Grand Slam | Hard |
| Tommy Haas | 3-6 6-3 2-6 | L | H2H | Match data | Aug 26, 2001* | F | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Thomas Johansson | 7-5 6-3 | W | H2H | Match data | Aug 25, 2001* | SF | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Felix Mantilla | 7-5 6-3 | W | H2H | Match data | Aug 25, 2001* | QF | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Alexander Peya | 6-3 6-2 | W | H2H | Match data | Aug 24, 2001* | R16 | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Olivier Rochus | 6-4 6-7(3) 7-6(4) | W | H2H | Match data | Aug 23, 2001* | R32 | Long Island | ATP International Series → modern equivalent ATP 250 | Hard |
| Alberto Martin | 4-6 4-6 | L | H2H | Match data | Aug 9, 2001* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Nicolas Lapentti | 6-3 6-2 | W | H2H | Match data | Aug 8, 2001* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Andre Agassi | 4-6 2-6 | L | H2H | Match data | Jul 29, 2001* | F | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Xavier Malisse | 7-6(4) 6-4 | W | H2H | Match data | Jul 28, 2001* | SF | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Magnus Norman | 7-5 7-6(4) | W | H2H | Match data | Jul 28, 2001* | QF | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Michael Chang | 7-6(6) 7-6(2) | W | H2H | Match data | Jul 27, 2001* | R16 | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Chris Woodruff | 7-5 6-2 | W | H2H | Match data | Jul 26, 2001* | R32 | Los Angeles Open | ATP International Series → modern equivalent ATP 250 | Hard |
| Roger Federer | 6-7(7) 7-5 4-6 7-6(2) 5-7 | L | H2H | Match data | Jul 4, 2001* | R16 | Wimbledon | Grand Slam | Grass |
| Sargis Sargsian | 6-4 6-4 7-5 | W | H2H | Match data | Jul 1, 2001* | R32 | Wimbledon | Grand Slam | Grass |
| Barry Cowan | 6-3 6-2 6-7(5) 4-6 6-3 | W | H2H | Match data | Jun 29, 2001* | R64 | Wimbledon | Grand Slam | Grass |
| Francisco Clavet | 6-4 7-6(5) 6-4 | W | H2H | Match data | Jun 27, 2001* | R128 | Wimbledon | Grand Slam | Grass |
| Lleyton Hewitt | 6-3 3-6 2-6 | L | H2H | Match data | Jun 16, 2001* | SF | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Jan-Michael Gambill | 7-6(1) 7-5 | W | H2H | Match data | Jun 16, 2001* | QF | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Jan Siemerink | 6-3 6-4 | W | H2H | Match data | Jun 15, 2001* | R16 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Olivier Rochus | 6-1 6-2 | W | H2H | Match data | Jun 14, 2001* | R32 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Galo Blanco | 6-7(4) 3-6 2-6 | L | H2H | Match data | Jun 1, 2001* | R64 | Roland Garros | Grand Slam | Clay |
| Cedric Kauffmann | 6-3 4-6 6-2 3-6 8-6 | W | H2H | Match data | May 30, 2001* | R128 | Roland Garros | Grand Slam | Clay |
| Alex Calatrava | 7-6(3) 3-6 4-6 | L | H2H | Match data | May 16, 2001* | R64 | Hamburg Open | Masters 1000 | Clay |
| Harel Levy | 5-7 6-2 4-6 | L | H2H | Match data | May 9, 2001* | R64 | Italian Open | Masters 1000 | Clay |
| Andy Roddick | 6-7(2) 3-6 | L | H2H | Match data | Mar 22, 2001* | R32 | Miami Open | Masters 1000 | Hard |
| Nicolas Kiefer | 6-3 3-6 6-3 | W | H2H | Match data | Mar 21, 2001* | R64 | Miami Open | Masters 1000 | Hard |
| Andre Agassi | 6-7(5) 5-7 1-6 | L | H2H | Match data | Mar 19, 2001* | F | Indian Wells Open | Masters 1000 | Hard |
| Yevgeny Kafelnikov | 7-5 6-4 | W | H2H | Match data | Mar 18, 2001* | SF | Indian Wells Open | Masters 1000 | Hard |
| Patrick Rafter | 4-6 7-6(4) 6-4 | W | H2H | Match data | Mar 18, 2001* | QF | Indian Wells Open | Masters 1000 | Hard |
| Sebastien Grosjean | 6-1 7-6(7) | W | H2H | Match data | Mar 17, 2001* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Fabrice Santoro | 6-3 3-6 6-0 | W | H2H | Match data | Mar 15, 2001* | R32 | Indian Wells Open | Masters 1000 | Hard |
| David Prinosil | 6-4 6-4 | W | H2H | Match data | Mar 14, 2001* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Andrew Ilie | 6-3 6-7(2) 4-6 | L | H2H | Match data | Mar 8, 2001* | R32 | Scottsdale | ATP International Series → modern equivalent ATP 250 | Hard |
| Chris Woodruff | 6-7(4) 2-6 | L | H2H | Match data | Feb 22, 2001* | R32 | Memphis | ATP International Series Gold → modern equivalent ATP 500 | Hard |
| Todd Martin | 7-6(2) 3-6 4-6 4-6 | L | H2H | Match data | Jan 24, 2001* | R16 | Australian Open | Grand Slam | Hard |
| Juan Ignacio Chela | 6-4 4-6 4-6 7-5 6-2 | W | H2H | Match data | Jan 21, 2001* | R32 | Australian Open | Grand Slam | Hard |
| Bohdan Ulihrach | 7-6(5) 7-6(5) 4-6 7-5 | W | H2H | Match data | Jan 19, 2001* | R64 | Australian Open | Grand Slam | Hard |
| Karol Kucera | 7-6(5) 3-6 6-4 7-6(3) | W | H2H | Match data | Jan 17, 2001* | R128 | Australian Open | Grand Slam | Hard |
| Gustavo Kuerten | 7-6(5) 3-6 4-6 | L | H2H | Match data | Dec 4, 2000* | SF | ATP Finals | ATP Finals | Hard |
| Lleyton Hewitt | 5-7 0-6 | L | H2H | Match data | Nov 27, 2000 | RR | ATP Finals | ATP Finals | Hard |
| Alex Corretja | 7-6(2) 7-5 | W | H2H | Match data | Nov 27, 2000 | RR | ATP Finals | ATP Finals | Hard |
| Marat Safin | 6-3 6-2 | W | H2H | Match data | Nov 27, 2000 | RR | ATP Finals | ATP Finals | Hard |
| Marat Safin | 4-6 3-6 3-6 | L | H2H | Match data | Sep 11, 2000* | F | US Open | Grand Slam | Hard |
| Lleyton Hewitt | 7-6(7) 6-4 7-6(5) | W | H2H | Match data | Sep 10, 2000* | SF | US Open | Grand Slam | Hard |
| Richard Krajicek | 4-6 7-6(6) 6-4 6-2 | W | H2H | Match data | Sep 8, 2000* | QF | US Open | Grand Slam | Hard |
| Hyung-Taik Lee | 7-6(4) 6-2 6-4 | W | H2H | Match data | Sep 6, 2000* | R16 | US Open | Grand Slam | Hard |
| Agustin Calleri | 7-6(5) 7-6(3) 6-3 | W | H2H | Match data | Sep 3, 2000* | R32 | US Open | Grand Slam | Hard |
| Justin Gimelstob | 6-3 6-1 6-3 | W | H2H | Match data | Sep 1, 2000* | R64 | US Open | Grand Slam | Hard |
| Martin Damm Sr | 7-6(3) 7-5 6-4 | W | — | Match data | Aug 30, 2000* | R128 | US Open | Grand Slam | Hard |
| Tim Henman | 3-6 4-6 | L | H2H | Match data | Aug 12, 2000* | R16 | Cincinnati Open | Masters 1000 | Hard |
| Taylor Dent | 7-6(3) 7-6(3) | W | H2H | Match data | Aug 10, 2000* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Mariano Zabaleta | 6-4 6-2 | W | H2H | Match data | Aug 9, 2000* | R64 | Cincinnati Open | Masters 1000 | Hard |
| Marat Safin | 4-6 6-3 6-7(8) | L | H2H | Match data | Aug 6, 2000* | QF | Canadian Open | Masters 1000 | Hard |
| Sargis Sargsian | 6-1 6-2 | W | H2H | Match data | Aug 5, 2000* | R16 | Canadian Open | Masters 1000 | Hard |
| Karim Alami | 7-6(3) 6-2 | W | H2H | Match data | Aug 3, 2000* | R32 | Canadian Open | Masters 1000 | Hard |
| Michael Llodra | 5-7 6-2 7-6(4) | W | H2H | Match data | Aug 2, 2000* | R64 | Canadian Open | Masters 1000 | Hard |
| Patrick Rafter | 6-7(10) 7-6(5) 6-4 6-2 | W | H2H | Match data | Jul 10, 2000* | F | Wimbledon | Grand Slam | Grass |
| Vladimir Voltchkov | 7-6(4) 6-2 6-4 | W | H2H | Match data | Jul 9, 2000* | SF | Wimbledon | Grand Slam | Grass |
| Jan-Michael Gambill | 6-4 6-7(4) 6-4 6-4 | W | H2H | Match data | Jul 7, 2000* | QF | Wimbledon | Grand Slam | Grass |
| Jonas Bjorkman | 6-3 6-2 7-5 | W | H2H | Match data | Jul 5, 2000* | R16 | Wimbledon | Grand Slam | Grass |
| Justin Gimelstob | 2-6 6-4 6-2 6-2 | W | H2H | Match data | Jul 2, 2000* | R32 | Wimbledon | Grand Slam | Grass |
| Karol Kucera | 7-6(9) 3-6 6-3 6-4 | W | H2H | Match data | Jun 30, 2000* | R64 | Wimbledon | Grand Slam | Grass |
| Jiri Vanek | 6-4 6-4 6-2 | W | H2H | Match data | Jun 28, 2000* | R128 | Wimbledon | Grand Slam | Grass |
| Lleyton Hewitt | 4-6 4-6 | L | H2H | Match data | Jun 18, 2000* | F | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Davide Sanguinetti | 7-5 6-3 | W | H2H | Match data | Jun 17, 2000* | SF | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Bob Bryan | 6-4 6-4 | W | H2H | Match data | Jun 17, 2000* | QF | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Michael Llodra | 6-1 7-6(2) | W | H2H | Match data | Jun 16, 2000* | R16 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Arvind Parmar | 6-7(8) 6-4 6-3 | W | H2H | Match data | Jun 15, 2000* | R32 | Queen's Club Championships | ATP International Series → modern equivalent ATP 250 | Grass |
| Mark Philippoussis | 6-4 5-7 6-7(4) 6-4 6-8 | L | H2H | Match data | May 31, 2000* | R128 | Roland Garros | Grand Slam | Clay |
| Arnaud Di Pasquale | 4-6 4-6 | L | H2H | Match data | May 18, 2000* | R32 | Hamburg Open | Masters 1000 | Clay |
| Chris Woodruff | 6-4 7-6(5) | W | H2H | Match data | May 17, 2000* | R64 | Hamburg Open | Masters 1000 | Clay |
| Gustavo Kuerten | 6-1 6-7(2) 7-6(5) 7-6(8) | W | H2H | Match data | Mar 27, 2000* | F | Miami Open | Masters 1000 | Hard |
| Lleyton Hewitt | 6-3 3-6 6-1 | W | H2H | Match data | Mar 26, 2000* | SF | Miami Open | Masters 1000 | Hard |
| Nicolas Lapentti | 6-4 7-6(3) | W | H2H | Match data | Mar 26, 2000* | QF | Miami Open | Masters 1000 | Hard |
| Greg Rusedski | 6-3 6-3 | W | H2H | Match data | Mar 25, 2000* | R16 | Miami Open | Masters 1000 | Hard |
| Andreas Vinciguerra | 5-7 7-6(3) 6-4 | W | H2H | Match data | Mar 23, 2000* | R32 | Miami Open | Masters 1000 | Hard |
| Carlos Moya | 6-1 6-4 | W | H2H | Match data | Mar 22, 2000* | R64 | Miami Open | Masters 1000 | Hard |
| Thomas Enqvist | 3-6 6-3 3-6 | L | H2H | Match data | Mar 19, 2000* | QF | Indian Wells Open | Masters 1000 | Hard |
| Byron Black | 4-6 6-3 6-2 | W | H2H | Match data | Mar 18, 2000* | R16 | Indian Wells Open | Masters 1000 | Hard |
| Wayne Ferreira | 3-6 7-6(4) 7-6(5) | W | H2H | Match data | Mar 16, 2000* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Andrei Medvedev | 6-4 6-3 | W | H2H | Match data | Mar 15, 2000* | R64 | Indian Wells Open | Masters 1000 | Hard |
| Alex Corretja | (w/o) | L | H2H | Match data | Mar 10, 2000* | R16 | Scottsdale | ATP International Series → modern equivalent ATP 250 | Hard |
| Greg Rusedski | 6-3 6-4 | W | H2H | Match data | Mar 9, 2000* | R32 | Scottsdale | ATP International Series → modern equivalent ATP 250 | Hard |
| Andre Agassi | 4-6 6-3 7-6(0) 6-7(5) 1-6 | L | H2H | Match data | Jan 30, 2000* | SF | Australian Open | Grand Slam | Hard |
| Chris Woodruff | 7-5 6-3 6-3 | W | H2H | Match data | Jan 28, 2000* | QF | Australian Open | Grand Slam | Hard |
| Slava Dosedel | 6-1 6-2 3-6 6-1 | W | H2H | Match data | Jan 26, 2000* | R16 | Australian Open | Grand Slam | Hard |
| Wayne Black | 6-7(9) 3-6 6-3 7-5 6-3 | W | H2H | Match data | Jan 23, 2000* | R32 | Australian Open | Grand Slam | Hard |
| Mikael Tillstrom | 6-3 7-6(6) 6-1 | W | H2H | Match data | Jan 21, 2000* | R64 | Australian Open | Grand Slam | Hard |
| Wayne Arthurs | 6-4 7-5 6-4 | W | H2H | Match data | Jan 19, 2000* | R128 | Australian Open | Grand Slam | Hard |
| Andre Agassi | 6-1 7-5 6-4 | W | H2H | Match data | Nov 30, 1999* | F | ATP Finals | ATP Finals | Hard |
| Nicolas Kiefer | 6-3 6-3 | W | H2H | Match data | Nov 29, 1999* | SF | ATP Finals | ATP Finals | Hard |
| Andre Agassi | 2-6 2-6 | L | H2H | Match data | Nov 22, 1999 | RR | ATP Finals | ATP Finals | Hard |
| Gustavo Kuerten | 6-2 6-3 | W | H2H | Match data | Nov 22, 1999 | RR | ATP Finals | ATP Finals | Hard |
| Nicolas Lapentti | 7-6(2) 7-6(5) | W | H2H | Match data | Nov 22, 1999 | RR | ATP Finals | ATP Finals | Hard |
| Tommy Haas | (w/o) | L | H2H | Match data | Nov 6, 1999* | R16 | Paris Masters | Masters 1000 | Carpet |
| Francisco Clavet | 4-6 6-3 7-6(4) | W | H2H | Match data | Nov 4, 1999* | R32 | Paris Masters | Masters 1000 | Carpet |
| Vincent Spadea | 4-6 6-3 (ret.) | L | H2H | Match data | Aug 21, 1999* | QF | Indianapolis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Max Mirnyi | 7-6(4) 6-3 | W | H2H | Match data | Aug 20, 1999* | R16 | Indianapolis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Guillaume Raoux | 6-4 7-5 | W | H2H | Match data | Aug 19, 1999* | R32 | Indianapolis | ATP Championship Series → modern equivalent ATP 500 | Hard |
| Patrick Rafter | 7-6(7) 6-3 | W | H2H | Match data | Aug 16, 1999* | F | Cincinnati Open | Masters 1000 | Hard |
| Andre Agassi | 7-6(7) 6-4 | W | H2H | Match data | Aug 15, 1999* | SF | Cincinnati Open | Masters 1000 | Hard |
| Richard Krajicek | 6-4 6-2 | W | H2H | Match data | Aug 15, 1999* | QF | Cincinnati Open | Masters 1000 | Hard |
| Rainer Schuettler | 7-5 7-6(2) | W | H2H | Match data | Aug 14, 1999* | R16 | Cincinnati Open | Masters 1000 | Hard |
| Jan Siemerink | 7-6(9) 6-4 | W | H2H | Match data | Aug 12, 1999* | R32 | Cincinnati Open | Masters 1000 | Hard |
| Andre Agassi | 7-6(3) 7-6(1) | W | H2H | Match data | Aug 1, 1999* | F | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| James Sekulov | 6-0 6-2 | W | H2H | Match data | Jul 31, 1999* | SF | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Wayne Ferreira | 4-6 6-3 6-3 | W | H2H | Match data | Jul 31, 1999* | QF | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Sebastien Lareau | 7-6(5) 6-3 | W | H2H | Match data | Jul 30, 1999* | R16 | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Phillip King | 6-1 6-2 | W | H2H | Match data | Jul 29, 1999* | R32 | Los Angeles Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Andre Agassi | 6-3 6-4 7-5 | W | H2H | Match data | Jul 5, 1999* | F | Wimbledon | Grand Slam | Grass |
| Tim Henman | 3-6 6-4 6-3 6-4 | W | H2H | Match data | Jul 4, 1999* | SF | Wimbledon | Grand Slam | Grass |
| Mark Philippoussis | 4-6 2-1 (ret.) | W | H2H | Match data | Jul 2, 1999* | QF | Wimbledon | Grand Slam | Grass |
| Daniel Nestor | 6-3 6-4 6-2 | W | H2H | Match data | Jun 30, 1999* | R16 | Wimbledon | Grand Slam | Grass |
| Danny Sapsford | 6-3 6-4 7-5 | W | H2H | Match data | Jun 27, 1999* | R32 | Wimbledon | Grand Slam | Grass |
| Sebastien Lareau | 6-4 6-2 6-3 | W | H2H | Match data | Jun 25, 1999* | R64 | Wimbledon | Grand Slam | Grass |
| Scott Draper | 6-3 6-4 6-4 | W | H2H | Match data | Jun 23, 1999* | R128 | Wimbledon | Grand Slam | Grass |
| Tim Henman | 6-7(1) 6-4 7-6(4) | W | H2H | Match data | Jun 13, 1999* | F | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Lleyton Hewitt | 4-6 6-4 7-6(4) | W | H2H | Match data | Jun 12, 1999* | SF | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Goran Ivanisevic | 7-5 6-4 | W | H2H | Match data | Jun 12, 1999* | QF | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Wayne Arthurs | 7-5 6-3 | W | H2H | Match data | Jun 11, 1999* | R16 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Todd Woodbridge | 6-4 6-7(8) 6-4 | W | H2H | Match data | Jun 10, 1999* | R32 | Queen's Club Championships | ATP World Series → modern equivalent ATP 250 | Grass |
| Andrei Medvedev | 5-7 6-1 4-6 3-6 | L | H2H | Match data | May 28, 1999* | R64 | Roland Garros | Grand Slam | Clay |
| Juan Antonio Marin | 6-7(5) 6-4 7-5 6-7(9) 6-4 | W | H2H | Match data | May 26, 1999* | R128 | Roland Garros | Grand Slam | Clay |
| Fernando Meligeni | 3-6 1-6 | L | H2H | Match data | May 13, 1999* | R32 | Italian Open | Masters 1000 | Clay |
| Bohdan Ulihrach | 3-6 6-2 7-6(2) | W | H2H | Match data | May 12, 1999* | R64 | Italian Open | Masters 1000 | Clay |
| Richard Krajicek | 2-6 6-7(6) | L | H2H | Match data | Mar 21, 1999* | QF | Miami Open | Masters 1000 | Hard |
| Albert Costa | 6-4 6-4 | W | H2H | Match data | Mar 20, 1999* | R16 | Miami Open | Masters 1000 | Hard |
| Jonas Bjorkman | 7-5 6-3 | W | H2H | Match data | Mar 18, 1999* | R32 | Miami Open | Masters 1000 | Hard |
| Jim Courier | 6-3 7-6(3) | W | H2H | Match data | Mar 17, 1999* | R64 | Miami Open | Masters 1000 | Hard |
| Felix Mantilla | 6-7(6) 6-3 3-6 | L | H2H | Match data | Mar 11, 1999* | R32 | Indian Wells Open | Masters 1000 | Hard |
| Jan-Michael Gambill | 6-4 3-6 4-6 | L | H2H | Match data | Mar 5, 1999* | R16 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Ramon Delgado | 7-6(2) 6-2 | W | H2H | Match data | Mar 4, 1999* | R32 | Scottsdale | ATP World Series → modern equivalent ATP 250 | Hard |
| Mark Philippoussis | (w/o) | L | H2H | Match data | Feb 13, 1999* | SF | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Bernd Karbacher | 7-5 6-3 | W | H2H | Match data | Feb 13, 1999* | QF | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Martin Rodriguez | 7-5 6-3 | W | H2H | Match data | Feb 12, 1999* | R16 | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Galo Blanco | 6-4 6-4 | W | H2H | Match data | Feb 11, 1999* | R32 | San Jose | ATP World Series → modern equivalent ATP 250 | Hard |
| Alex Corretja | 6-4 3-6 6-7(3) | L | H2H | Match data | Nov 30, 1998* | SF | ATP Finals | ATP Finals | Hard |
| Carlos Moya | 6-3 6-3 | W | H2H | Match data | Nov 23, 1998 | RR | ATP Finals | ATP Finals | Hard |
| Karol Kucera | 6-2 6-1 | W | H2H | Match data | Nov 23, 1998 | RR | ATP Finals | ATP Finals | Hard |
| Yevgeny Kafelnikov | 6-2 6-4 | W | H2H | Match data | Nov 23, 1998 | RR | ATP Finals | ATP Finals | Hard |
| Jason Stoltenberg | 6-7(5) 6-4 4-6 | L | H2H | Match data | Nov 12, 1998* | R32 | Stockholm Open | ATP World Series → modern equivalent ATP 250 | Hard |
| Greg Rusedski | 4-6 6-7(4) 3-6 | L | H2H | Match data | Nov 9, 1998* | F | Paris Masters | Masters 1000 | Carpet |
| Todd Martin | 6-4 7-6(5) | W | H2H | Match data | Nov 8, 1998* | SF | Paris Masters | Masters 1000 | Carpet |
| Mark Philippoussis | 6-3 6-3 | W | H2H | Match data | Nov 8, 1998* | QF | Paris Masters | Masters 1000 | Carpet |
| Jerome Golmard | 6-7(4) 6-4 6-4 | W | H2H | Match data | Nov 7, 1998* | R16 | Paris Masters | Masters 1000 | Carpet |
| Thomas Johansson | 7-6(7) 6-1 | W | H2H | Match data | Nov 5, 1998* | R32 | Paris Masters | Masters 1000 | Carpet |
| Richard Krajicek | 7-6(2) 4-6 6-7(5) | L | H2H | Match data | Nov 1, 1998* | SF | Stuttgart Masters | Masters 1000 | Hard |
| Jan-Michael Gambill | 4-1 (ret.) | W | H2H | Match data | Nov 1, 1998* | QF | Stuttgart Masters | Masters 1000 | Hard |
| Bohdan Ulihrach | 6-3 6-3 | W | H2H | Match data | Oct 31, 1998* | R16 | Stuttgart Masters | Masters 1000 | Hard |
| Nicolas Kiefer | 6-3 6-4 | W | H2H | Match data | Oct 29, 1998* | R32 | Stuttgart Masters | Masters 1000 | Hard |
| Tommy Haas | (w/o) | L | H2H | Match data | Oct 24, 1998* | QF | Montpellier Open | ATP World Series → modern equivalent ATP 250 | Carpet |
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.