Match log updated: 2026-05-28 18:14 UTC
Nicolas Lapentti — ATP Match Log
Main draw matches: 562 | W: 282 | L: 280 | Win %: 50.2%
44 qualifying matches shown below; qualifying is excluded from main-draw summaries and leaderboards.
| Date ↑ | Tournament | Category | Round | Surface | Opponent | Score | Result | H2H | Match |
|---|---|---|---|---|---|---|---|---|---|
| Sep 14, 1995* | Bogota | ATP 250 | R32 | Clay | Juan Albert Viloca Puig | 6-4 6-4 | W | — | Match data |
| Sep 15, 1995* | Bogota | ATP 250 | R16 | Clay | Steve Campbell | 7-6(2) 6-2 | W | H2H | Match data |
| Sep 16, 1995* | Bogota | ATP 250 | QF | Clay | Marcelo Rios | 6-3 6-4 | W | H2H | Match data |
| Sep 16, 1995* | Bogota | ATP 250 | SF | Clay | Luis Adrian Morejon | 7-5 6-7(0) 7-5 | W | H2H | Match data |
| Sep 17, 1995* | Bogota | ATP 250 | F | Clay | Miguel Tobon | 2-6 6-1 6-4 | W | H2H | Match data |
| Jan 11, 1996* | Jakarta | ATP 250 | R32 | Hard | Frederik Fetterlein | 6-3 6-1 | W | H2H | Match data |
| Jan 12, 1996* | Jakarta | ATP 250 | R16 | Hard | Sjeng Schalken | 3-6 6-4 1-6 | L | H2H | Match data |
| Jan 17, 1996* | Australian Open | Grand Slam | R128 | Hard | Magnus Larsson | 7-6(1) 3-6 6-7(3) 3-6 | L | H2H | Match data |
| Feb 21, 1996* | Memphis | ATP 250 | R64 | Hard | Lionel Roux | 1-6 7-6(5) 4-6 | L | H2H | Match data |
| Mar 7, 1996* | Mexico City | ATP 250 | R32 | Clay | Frederic Fontang | 6-7(4) 7-6(5) 2-6 | L | H2H | Match data |
| Mar 13, 1996* | Indian Wells Masters | Masters 1000 | R64 | Hard | Sjeng Schalken | 6-7(4) 3-6 | L | H2H | Match data |
| Mar 19, 1996* | Miami Masters | Masters 1000 | R128 | Hard | Marcos Ondruska | 2-6 6-4 2-6 | L | H2H | Match data |
| Apr 18, 1996* | Bermuda | ATP 250 | R32 | Clay | Karel Novacek | 7-5 3-6 6-4 | W | H2H | Match data |
| Apr 19, 1996* | Bermuda | ATP 250 | R16 | Clay | Dirk Dier | 2-6 4-6 | L | H2H | Match data |
| May 16, 1996* | Coral Springs | ATP 250 | R32 | Clay | Wade Mcguire | 5-7 7-6(9) 7-6(8) | W | H2H | Match data |
| May 17, 1996* | Coral Springs | ATP 250 | R16 | Clay | Vincent Spadea | 5-7 6-4 2-4 (ret.) | L | H2H | Match data |
| May 29, 1996* | Roland Garros | Grand Slam | R128 | Clay | Andrei Medvedev | 2-6 2-6 3-6 | L | H2H | Match data |
| Jun 13, 1996* | Oporto | ATP 250 | R32 | Clay | Francisco Roig | 3-6 7-6(6) 6-1 | W | H2H | Match data |
| Jun 14, 1996* | Oporto | ATP 250 | R16 | Clay | Richard Fromberg | 2-6 5-7 | L | H2H | Match data |
| Jun 20, 1996* | Nottingham | ATP 250 | R32 | Grass | Chris Woodruff | 5-7 5-7 | L | H2H | Match data |
| Jun 26, 1996* | Wimbledon | Grand Slam | R128 | Grass | Kenneth Carlsen | 7-6(3) 3-6 6-7(6) 6-4 6-4 | W | H2H | Match data |
| Jun 28, 1996* | Wimbledon | Grand Slam | R64 | Grass | Luke Milligan | 4-6 2-6 7-6(5) 7-6(3) 1-6 | L | H2H | Match data |
| Jul 11, 1996* | Bastad | ATP 250 | R32 | Clay | Jerome Golmard | 6-2 2-6 6-1 | W | H2H | Match data |
| Jul 12, 1996* | Bastad | ATP 250 | R16 | Clay | Tomas Carbonell | 2-6 5-7 | L | H2H | Match data |
| Aug 22, 1996* | Long Island | ATP 250 | R32 | Hard | Younes El Aynaoui | 4-6 3-6 | L | H2H | Match data |
| Aug 28, 1996* | US Open | Grand Slam | R128 | Hard | Alex Obrien | 4-6 6-1 4-6 3-6 | L | — | Match data |
| Sep 12, 1996* | Bogota | ATP 250 | R32 | Clay | David Rikl | 6-4 4-6 6-4 | W | H2H | Match data |
| Sep 13, 1996* | Bogota | ATP 250 | R16 | Clay | Wayne Black | 6-2 6-2 | W | H2H | Match data |
| Sep 14, 1996* | Bogota | ATP 250 | QF | Clay | Alejandro Hernandez | 7-6(5) 6-4 | W | — | Match data |
| Sep 14, 1996* | Bogota | ATP 250 | SF | Clay | Mauricio Hadad | 4-6 6-3 7-5 | W | H2H | Match data |
| Sep 15, 1996* | Bogota | ATP 250 | F | Clay | Thomas Muster | 7-6(6) 2-6 3-6 | L | H2H | Match data |
| Oct 3, 1996* | Marbella | ATP 250 | R32 | Clay | Alex Corretja | 4-6 6-7(2) | L | H2H | Match data |
| Oct 17, 1996* | Ostrava | ATP 250 | R32 | Carpet | Petr Korda | 3-6 2-6 | L | H2H | Match data |
| Nov 7, 1996* | Santiago | ATP 250 | R32 | Clay | Gabriel Markus | 6-4 6-4 | W | H2H | Match data |
| Nov 8, 1996* | Santiago | ATP 250 | R16 | Clay | Hernan Gumy | 4-6 7-6(1) 6-7(4) | L | H2H | Match data |
| Feb 13, 1997* | San Jose | ATP 250 | R32 | Hard | Sargis Sargsian | 4-6 1-6 | L | H2H | Match data |
| Feb 20, 1997* | Memphis | ATP 250 | R32 | Hard | Brett Steven | 6-7(2) 4-6 | L | H2H | Match data |
| Mar 19, 1997* | Miami Masters | Masters 1000 | R64 | Hard | Chris Woodruff | 3-6 3-6 | L | H2H | Match data |
| May 1, 1997* | Prague | ATP 250 | R32 | Clay | Carlos Costa | 6-2 6-7(3) 6-7(4) | L | H2H | Match data |
| May 28, 1997* | Roland Garros | Grand Slam | R128 | Clay | Frederik Fetterlein | 6-4 6-1 6-2 | W | H2H | Match data |
| May 30, 1997* | Roland Garros | Grand Slam | R64 | Clay | Chris Woodruff | 4-6 7-5 6-3 4-6 1-6 | L | H2H | Match data |
| Jun 12, 1997* | Bologna | ATP 250 | R32 | Clay | Carlos Costa | 6-4 3-1 (ret.) | W | H2H | Match data |
| Jun 13, 1997* | Bologna | ATP 250 | R16 | Clay | Davide Scala | 6-7(7) 6-4 6-3 | W | H2H | Match data |
| Jun 14, 1997* | Bologna | ATP 250 | QF | Clay | Felix Mantilla | 6-4 4-6 3-6 | L | H2H | Match data |
| Jun 25, 1997* | Wimbledon | Grand Slam | R128 | Grass | Francisco Clavet | 5-7 1-6 3-6 | L | H2H | Match data |
| Jul 23, 1997* | Kitzbuhel | ATP 250 | R64 | Clay | Emilio Sanchez | 2-6 6-1 6-1 | W | H2H | Match data |
| Jul 24, 1997* | Kitzbuhel | ATP 250 | R32 | Clay | Jeff Tarango | 6-3 3-6 6-1 | W | H2H | Match data |
| Jul 25, 1997* | Kitzbuhel | ATP 250 | R16 | Clay | Stefan Koubek | 5-7 3-6 | L | H2H | Match data |
| Aug 7, 1997* | San Marino | ATP 250 | R32 | Clay | Hendrik Dreekmann | 6-3 3-6 2-6 | L | H2H | Match data |
| Aug 13, 1997* | New Haven | ATP 250 | R64 | Hard | Sjeng Schalken | 6-1 (ret.) | W | H2H | Match data |
| Aug 14, 1997* | New Haven | ATP 250 | R32 | Hard | Richard Krajicek | 4-6 3-6 | L | H2H | Match data |
| Aug 21, 1997* | Long Island | ATP 250 | R32 | Hard | Jan Siemerink | 7-6(4) 6-4 | W | H2H | Match data |
| Aug 22, 1997* | Long Island | ATP 250 | R16 | Hard | Goran Ivanisevic | 7-5 2-6 6-7(4) | L | H2H | Match data |
| Aug 27, 1997* | US Open | Grand Slam | R128 | Hard | Andrei Pavel | 6-4 5-0 (ret.) | W | H2H | Match data |
| Aug 29, 1997* | US Open | Grand Slam | R64 | Hard | Cedric Pioline | 0-6 4-6 2-6 | L | H2H | Match data |
| Sep 11, 1997* | Marbella | ATP 250 | R32 | Clay | Dominik Hrbaty | 3-6 2-6 | L | H2H | Match data |
| Sep 25, 1997* | Bucharest | ATP 250 | R32 | Clay | Emilio Benfele Alvarez | 6-4 6-3 | W | H2H | Match data |
| Sep 26, 1997* | Bucharest | ATP 250 | R16 | Clay | Alberto Berasategui | 7-6(5) 6-3 | W | H2H | Match data |
| Sep 27, 1997* | Bucharest | ATP 250 | QF | Clay | Andrea Gaudenzi | 2-6 4-6 | L | H2H | Match data |
| Oct 2, 1997* | Palermo | ATP 250 | R32 | Clay | Richard Fromberg | 1-6 7-6(3) 3-6 | L | H2H | Match data |
| Oct 23, 1997* | Mexico City | ATP 250 | R32 | Clay | Oleg Ogorodov | 6-2 6-2 | W | H2H | Match data |
| Oct 24, 1997* | Mexico City | ATP 250 | R16 | Clay | Galo Blanco | 6-3 6-0 | W | H2H | Match data |
| Oct 25, 1997* | Mexico City | ATP 250 | QF | Clay | Emilio Benfele Alvarez | 6-2 4-6 7-5 | W | H2H | Match data |
| Oct 25, 1997* | Mexico City | ATP 250 | SF | Clay | Francisco Clavet | 5-7 6-7(5) | L | H2H | Match data |
| Oct 30, 1997* | Bogota | ATP 250 | R32 | Clay | Andrei Pavel | 6-2 6-2 | W | H2H | Match data |
| Oct 31, 1997* | Bogota | ATP 250 | R16 | Clay | Mario Rincon | 6-3 6-3 | W | H2H | Match data |
| Nov 1, 1997* | Bogota | ATP 250 | QF | Clay | Carlos Costa | 7-5 4-6 6-3 | W | H2H | Match data |
| Nov 1, 1997* | Bogota | ATP 250 | SF | Clay | Vincent Spadea | 6-2 7-5 | W | H2H | Match data |
| Nov 2, 1997* | Bogota | ATP 250 | F | Clay | Francisco Clavet | 3-6 3-6 | L | H2H | Match data |
| Nov 6, 1997* | Santiago | ATP 250 | R32 | Clay | Sebastian Prieto | 4-6 4-6 | L | H2H | Match data |
| Jan 15, 1998* | Auckland | ATP 250 | R32 | Hard | Marcelo Rios | 3-6 3-6 | L | H2H | Match data |
| Jan 21, 1998* | Australian Open | Grand Slam | R128 | Hard | Juan Albert Viloca Puig | 5-7 6-3 6-4 6-7(3) 6-1 | W | — | Match data |
| Jan 23, 1998* | Australian Open | Grand Slam | R64 | Hard | Fabrice Santoro | 4-6 6-3 6-3 2-6 4-6 | L | H2H | Match data |
| Feb 18, 1998* | Memphis | ATP 250 | R64 | Hard | Tomas Nydahl | 3-6 6-7(5) | L | H2H | Match data |
| Feb 26, 1998* | Philadelphia | ATP 250 | R32 | Hard | Marcello Craca | 4-6 4-6 | L | H2H | Match data |
| Mar 5, 1998* | Scottsdale | ATP 250 | R32 | Hard | Javier Sanchez | 3-6 6-3 6-2 | W | H2H | Match data |
| Mar 6, 1998* | Scottsdale | ATP 250 | R16 | Hard | Andre Agassi | 5-7 1-6 | L | H2H | Match data |
| Mar 12, 1998* | Indian Wells Masters | Masters 1000 | R32 | Hard | Wayne Black | 1-6 6-3 6-0 | W | H2H | Match data |
| Mar 14, 1998* | Indian Wells Masters | Masters 1000 | R16 | Hard | Andrei Medvedev | 1-6 4-6 | L | H2H | Match data |
| Mar 17, 1998* | Miami Masters | Masters 1000 | R128 | Hard | Slava Dosedel | 6-3 6-7(11) 4-6 | L | H2H | Match data |
| Apr 15, 1998* | Barcelona | ATP 250 | R64 | Clay | Albert Costa | 6-4 3-6 1-6 | L | H2H | Match data |
| Apr 22, 1998* | Monte Carlo Masters | Masters 1000 | R64 | Clay | Sebastien Grosjean | 2-6 4-6 | L | H2H | Match data |
| Apr 30, 1998* | Prague | ATP 250 | R32 | Clay | Bohdan Ulihrach | 6-4 6-4 | W | H2H | Match data |
| May 1, 1998* | Prague | ATP 250 | R16 | Clay | Martin Sinner | 6-2 6-0 | W | H2H | Match data |
| May 2, 1998* | Prague | ATP 250 | QF | Clay | Fernando Vicente | 6-0 7-5 | W | H2H | Match data |
| May 2, 1998* | Prague | ATP 250 | SF | Clay | Slava Dosedel | 6-3 3-6 2-6 | L | H2H | Match data |
| May 6, 1998* | Hamburg Masters | Masters 1000 | R64 | Clay | Brett Steven | 6-4 6-4 | W | H2H | Match data |
| May 7, 1998* | Hamburg Masters | Masters 1000 | R32 | Clay | Goran Ivanisevic | 6-4 1-6 4-6 | L | H2H | Match data |
| May 13, 1998* | Rome Masters | Masters 1000 | R64 | Clay | Gianluca Pozzi | 7-6(1) 6-4 | W | H2H | Match data |
| May 14, 1998* | Rome Masters | Masters 1000 | R32 | Clay | Gustavo Kuerten | 0-6 5-7 | L | H2H | Match data |
| May 21, 1998* | St. Poelten | ATP 250 | R32 | Clay | Juan Antonio Marin | 5-7 3-6 | L | H2H | Match data |
| May 27, 1998* | Roland Garros | Grand Slam | R128 | Clay | Richard Krajicek | 4-6 4-6 7-6(2) 6-7(5) | L | H2H | Match data |
| Jun 18, 1998* | Nottingham | ATP 250 | R32 | Grass | Byron Black | 0-6 2-6 | L | H2H | Match data |
| Jun 24, 1998* | Wimbledon | Grand Slam | R128 | Grass | David Prinosil | 6-4 3-6 4-6 3-6 | L | H2H | Match data |
| Jul 9, 1998* | Gstaad | ATP 250 | R32 | Clay | Cedric Pioline | 4-6 4-6 | L | H2H | Match data |
| Jul 22, 1998* | Stuttgart Outdoor | ATP 250 | R64 | Clay | Franco Squillari | 2-6 6-3 1-6 | L | H2H | Match data |
| Jul 30, 1998* | Kitzbuhel | ATP 250 | R32 | Clay | Fernando Vicente | 6-4 6-1 | W | H2H | Match data |
| Jul 31, 1998* | Kitzbuhel | ATP 250 | R16 | Clay | Yevgeny Kafelnikov | 6-4 6-1 | W | H2H | Match data |
| Aug 1, 1998* | Kitzbuhel | ATP 250 | QF | Clay | Andrea Gaudenzi | 3-6 6-7(5) | L | H2H | Match data |
| Aug 12, 1998* | Cincinnati Masters | Masters 1000 | R64 | Hard | Scott Draper | 4-6 6-4 5-7 | L | H2H | Match data |
| Aug 19, 1998* | New Haven | ATP 250 | R64 | Hard | Jan Siemerink | 4-6 3-6 | L | H2H | Match data |
| Aug 27, 1998* | Boston | ATP 250 | R32 | Hard | Carlos Costa | 6-7(8) 6-4 7-5 | W | H2H | Match data |
| Aug 28, 1998* | Boston | ATP 250 | R16 | Hard | Thomas Muster | 2-6 4-6 | L | H2H | Match data |
| Sep 2, 1998* | US Open | Grand Slam | R128 | Hard | Fabrice Santoro | 6-4 5-7 3-6 6-3 6-7(4) | L | H2H | Match data |
| Sep 17, 1998* | Bucharest | ATP 250 | R32 | Clay | Jan Apell | 6-3 6-4 | W | H2H | Match data |
| Sep 18, 1998* | Bucharest | ATP 250 | R16 | Clay | Arnaud Di Pasquale | 2-6 7-6(7) 1-6 | L | — | Match data |
| Oct 1, 1998* | Mallorca | ATP 250 | R32 | Clay | Alberto Berasategui | 2-6 4-6 | L | H2H | Match data |
| Oct 8, 1998* | Palermo | ATP 250 | R32 | Clay | Jiri Novak | 6-3 7-5 | W | H2H | Match data |
| Oct 9, 1998* | Palermo | ATP 250 | R16 | Clay | Massimo Valeri | 7-6(4) 7-5 | W | H2H | Match data |
| Oct 10, 1998* | Palermo | ATP 250 | QF | Clay | Alex Corretja | 5-7 2-6 | L | H2H | Match data |
| Oct 29, 1998* | Mexico City | ATP 250 | R32 | Clay | Jordi Burillo | 1-6 4-6 | L | H2H | Match data |
| Nov 5, 1998* | Bogota | ATP 250 | R32 | Clay | Juan Balcells | 3-6 6-7(2) | L | H2H | Match data |
| Nov 12, 1998* | Santiago | ATP 250 | R32 | Clay | Carlos Costa | 4-6 6-3 6-3 | W | H2H | Match data |
| Nov 13, 1998* | Santiago | ATP 250 | R16 | Clay | Gustavo Kuerten | 7-6(3) 6-3 | W | H2H | Match data |
| Nov 14, 1998* | Santiago | ATP 250 | QF | Clay | Francisco Clavet | 4-6 4-6 | L | H2H | Match data |
| Jan 20, 1999* | Australian Open | Grand Slam | R128 | Hard | Thomas Johansson | 6-3 3-6 3-6 7-6(4) 6-0 | W | H2H | Match data |
| Jan 22, 1999* | Australian Open | Grand Slam | R64 | Hard | Magnus Norman | 7-6(4) 3-6 2-6 6-3 6-4 | W | H2H | Match data |
| Jan 24, 1999* | Australian Open | Grand Slam | R32 | Hard | Mikael Tillstrom | 4-6 7-6(9) 2-6 6-4 6-2 | W | H2H | Match data |
| Jan 27, 1999* | Australian Open | Grand Slam | R16 | Hard | Andrew Ilie | 6-4 6-2 4-6 6-2 | W | H2H | Match data |
| Jan 29, 1999* | Australian Open | Grand Slam | QF | Hard | Karol Kucera | 7-6(4) 6-7(6) 6-2 0-6 8-6 | W | H2H | Match data |
| Jan 31, 1999* | Australian Open | Grand Slam | SF | Hard | Thomas Enqvist | 3-6 5-7 1-6 | L | H2H | Match data |
| Mar 4, 1999* | Scottsdale | ATP 250 | R32 | Hard | Andrei Pavel | 6-3 4-6 6-1 | W | H2H | Match data |
| Mar 5, 1999* | Scottsdale | ATP 250 | R16 | Hard | Jerome Golmard | 5-3 (ret.) | L | H2H | Match data |
| Mar 16, 1999* | Miami Masters | Masters 1000 | R128 | Hard | Mikael Tillstrom | 6-0 6-2 | W | H2H | Match data |
| Mar 17, 1999* | Miami Masters | Masters 1000 | R64 | Hard | Tommy Haas | 5-7 7-6(3) 6-2 | W | H2H | Match data |
| Mar 18, 1999* | Miami Masters | Masters 1000 | R32 | Hard | Albert Costa | 6-7(3) 4-6 | L | H2H | Match data |
| Apr 21, 1999* | Monte Carlo Masters | Masters 1000 | R64 | Clay | Andrea Gaudenzi | 6-1 7-6(1) | W | H2H | Match data |
| Apr 22, 1999* | Monte Carlo Masters | Masters 1000 | R32 | Clay | Felix Mantilla | 5-7 6-7(4) | L | H2H | Match data |
| Apr 29, 1999* | Prague | ATP 250 | R32 | Clay | Radovan Svetlik | 6-0 6-4 | W | H2H | Match data |
| Apr 30, 1999* | Prague | ATP 250 | R16 | Clay | Orlin Stanoytchev | 6-3 6-7(3) 4-6 | L | H2H | Match data |
| May 5, 1999* | Hamburg Masters | Masters 1000 | R64 | Clay | Lars Burgsmuller | 6-4 6-3 | W | H2H | Match data |
| May 6, 1999* | Hamburg Masters | Masters 1000 | R32 | Clay | Marc Rosset | 6-2 6-0 | W | H2H | Match data |
| May 8, 1999* | Hamburg Masters | Masters 1000 | R16 | Clay | Hicham Arazi | 6-4 6-0 | W | H2H | Match data |
| May 9, 1999* | Hamburg Masters | Masters 1000 | QF | Clay | Arnaud Di Pasquale | 6-4 6-7(6) 6-2 | W | — | Match data |
| May 9, 1999* | Hamburg Masters | Masters 1000 | SF | Clay | Mariano Zabaleta | 5-7 2-6 | L | H2H | Match data |
| May 12, 1999* | Rome Masters | Masters 1000 | R64 | Clay | Albert Portas | 6-7(5) 6-4 6-2 | W | H2H | Match data |
| May 13, 1999* | Rome Masters | Masters 1000 | R32 | Clay | Greg Rusedski | 6-3 6-3 | W | H2H | Match data |
| May 15, 1999* | Rome Masters | Masters 1000 | R16 | Clay | Nicolas Kiefer | 3-6 7-6(3) 6-3 | W | H2H | Match data |
| May 16, 1999* | Rome Masters | Masters 1000 | QF | Clay | Patrick Rafter | 6-4 5-7 1-6 | L | H2H | Match data |
| May 26, 1999* | Roland Garros | Grand Slam | R128 | Clay | Thomas Muster | 2-6 6-1 6-2 7-6(4) | W | H2H | Match data |
| May 28, 1999* | Roland Garros | Grand Slam | R64 | Clay | Chris Woodruff | 6-7(2) 6-7(5) 5-7 | L | H2H | Match data |
| Jun 23, 1999* | Wimbledon | Grand Slam | R128 | Grass | Adrian Voinea | 7-6(8) 6-3 4-6 2-6 8-6 | W | H2H | Match data |
| Jun 25, 1999* | Wimbledon | Grand Slam | R64 | Grass | Wayne Arthurs | 5-7 6-7(7) 5-7 | L | H2H | Match data |
| Jul 8, 1999* | Gstaad | ATP 250 | R32 | Clay | Alex Corretja | 4-3 (ret.) | W | H2H | Match data |
| Jul 9, 1999* | Gstaad | ATP 250 | R16 | Clay | Ivan Ljubicic | 6-4 2-6 6-3 | W | H2H | Match data |
| Jul 10, 1999* | Gstaad | ATP 250 | QF | Clay | Andrea Gaudenzi | 7-5 6-3 | W | H2H | Match data |
| Jul 10, 1999* | Gstaad | ATP 250 | SF | Clay | Felix Mantilla | 6-4 4-6 7-5 | W | H2H | Match data |
| Jul 11, 1999* | Gstaad | ATP 250 | F | Clay | Albert Costa | 6-7(4) 3-6 4-6 | L | H2H | Match data |
| Jul 22, 1999* | Stuttgart Outdoor | ATP 250 | R32 | Clay | Stefan Koubek | 6-4 6-4 | W | H2H | Match data |
| Jul 23, 1999* | Stuttgart Outdoor | ATP 250 | R16 | Clay | Dominik Hrbaty | 7-5 6-3 | W | H2H | Match data |
| Jul 24, 1999* | Stuttgart Outdoor | ATP 250 | QF | Clay | Magnus Norman | 6-7(5) 6-4 2-6 | L | H2H | Match data |
| Jul 29, 1999* | Kitzbuhel | ATP 250 | R32 | Clay | Markus Hipfl | 6-3 6-0 | W | H2H | Match data |
| Jul 30, 1999* | Kitzbuhel | ATP 250 | R16 | Clay | Wolfgang Schranz | 6-4 6-3 | W | H2H | Match data |
| Jul 31, 1999* | Kitzbuhel | ATP 250 | QF | Clay | Fernando Vicente | 7-6(4) 1-6 3-6 | L | H2H | Match data |
| Aug 5, 1999* | Amsterdam | ATP 250 | R32 | Clay | Martin Rodriguez | 6-3 6-2 | W | H2H | Match data |
| Aug 6, 1999* | Amsterdam | ATP 250 | R16 | Clay | Christian Ruud | 7-5 6-3 | W | H2H | Match data |
| Aug 7, 1999* | Amsterdam | ATP 250 | QF | Clay | Hicham Arazi | 2-6 7-5 6-3 | W | H2H | Match data |
| Aug 7, 1999* | Amsterdam | ATP 250 | SF | Clay | Mariano Zabaleta | 6-3 5-7 5-7 | L | H2H | Match data |
| Aug 11, 1999* | Cincinnati Masters | Masters 1000 | R64 | Hard | Vincent Spadea | 6-2 6-2 | W | H2H | Match data |
| Aug 12, 1999* | Cincinnati Masters | Masters 1000 | R32 | Hard | Jan-Michael Gambill | 6-0 7-6(3) | W | H2H | Match data |
| Aug 14, 1999* | Cincinnati Masters | Masters 1000 | R16 | Hard | Patrick Rafter | 2-6 3-6 | L | H2H | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | R64 | Hard | Grant Stafford | 6-3 7-5 | W | H2H | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | R32 | Hard | Jared Palmer | 6-2 6-2 | W | H2H | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | R16 | Hard | Arnaud Di Pasquale | 6-4 7-6(5) | W | — | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | QF | Hard | Carlos Moya | 6-1 6-2 | W | H2H | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | SF | Hard | Jan Siemerink | 6-4 6-2 | W | H2H | Match data |
| Aug 16, 1999 | Indianapolis | ATP 250 | F | Hard | Vincent Spadea | 4-6 6-4 6-4 | W | H2H | Match data |
| Sep 1, 1999* | US Open | Grand Slam | R128 | Hard | Francisco Clavet | 6-3 7-5 4-6 6-4 | W | H2H | Match data |
| Sep 3, 1999* | US Open | Grand Slam | R64 | Hard | Fredrik Jonsson | 4-6 7-5 4-6 5-7 | L | H2H | Match data |
| Oct 1, 1999* | Grand Slam Cup | ATP Finals | R16 | Hard | Fernando Meligeni | 6-4 2-6 16-14 | W | H2H | Match data |
| Oct 2, 1999* | Grand Slam Cup | ATP Finals | QF | Hard | Thomas Enqvist | 3-6 2-6 | L | H2H | Match data |
| Oct 7, 1999* | Basel | ATP 250 | R32 | Carpet | Hicham Arazi | 3-6 6-3 3-6 | L | H2H | Match data |
| Oct 14, 1999* | Vienna | ATP 250 | R32 | Hard | Francisco Clavet | 7-6(1) 6-2 | W | H2H | Match data |
| Oct 15, 1999* | Vienna | ATP 250 | R16 | Hard | Karol Kucera | 2-6 3-6 | L | H2H | Match data |
| Oct 21, 1999* | Lyon | ATP 250 | R32 | Carpet | Jan Siemerink | 3-6 6-3 7-6(4) | W | H2H | Match data |
| Oct 22, 1999* | Lyon | ATP 250 | R16 | Carpet | Sebastien Grosjean | 4-6 6-4 6-1 | W | H2H | Match data |
| Oct 23, 1999* | Lyon | ATP 250 | QF | Carpet | Gustavo Kuerten | 5-7 6-4 7-5 | W | H2H | Match data |
| Oct 23, 1999* | Lyon | ATP 250 | SF | Carpet | Magnus Gustafsson | 6-7(5) 7-6(6) 6-2 | W | H2H | Match data |
| Oct 24, 1999* | Lyon | ATP 250 | F | Carpet | Lleyton Hewitt | 6-3 6-2 | W | H2H | Match data |
| Oct 28, 1999* | Stuttgart Masters | Masters 1000 | R32 | Hard | Dominik Hrbaty | 3-6 6-4 6-3 | W | H2H | Match data |
| Oct 30, 1999* | Stuttgart Masters | Masters 1000 | R16 | Hard | Marcelo Rios | 4-6 3-6 | L | H2H | Match data |
| Nov 4, 1999* | Paris Masters | Masters 1000 | R32 | Carpet | Fabrice Santoro | 6-3 7-6(5) | W | H2H | Match data |
| Nov 6, 1999* | Paris Masters | Masters 1000 | R16 | Carpet | Albert Costa | 6-2 7-5 | W | H2H | Match data |
| Nov 7, 1999* | Paris Masters | Masters 1000 | QF | Carpet | Tommy Haas | 6-4 3-6 6-3 | W | H2H | Match data |
| Nov 7, 1999* | Paris Masters | Masters 1000 | SF | Carpet | Andre Agassi | 6-3 3-6 2-6 | L | H2H | Match data |
| Nov 11, 1999* | Stockholm | ATP 250 | R32 | Hard | Peter Wessels | 6-4 7-6(5) | W | H2H | Match data |
| Nov 12, 1999* | Stockholm | ATP 250 | R16 | Hard | Filip Dewulf | 5-7 6-3 6-3 | W | H2H | Match data |
| Nov 13, 1999* | Stockholm | ATP 250 | QF | Hard | Magnus Norman | 1-6 4-6 | L | H2H | Match data |
| Nov 22, 1999 | Tour Finals | ATP Finals | RR | Hard | Andre Agassi | 1-6 2-6 | L | H2H | Match data |
| Nov 22, 1999 | Tour Finals | ATP Finals | RR | Hard | Pete Sampras | 6-7(2) 6-7(5) | L | H2H | Match data |
| Nov 22, 1999 | Tour Finals | ATP Finals | RR | Hard | Gustavo Kuerten | 1-6 2-6 | L | H2H | Match data |
| Jan 13, 2000* | Sydney | ATP 250 | R32 | Hard | Younes El Aynaoui | 3-6 6-3 6-3 | W | H2H | Match data |
| Jan 14, 2000* | Sydney | ATP 250 | R16 | Hard | Stefan Koubek | 4-6 6-0 6-4 | W | H2H | Match data |
| Jan 15, 2000* | Sydney | ATP 250 | QF | Hard | Jason Stoltenberg | 6-4 5-7 1-6 | L | H2H | Match data |
| Jan 19, 2000* | Australian Open | Grand Slam | R128 | Hard | Andrei Medvedev | 6-3 5-7 6-7(2) 6-4 8-6 | W | H2H | Match data |
| Jan 21, 2000* | Australian Open | Grand Slam | R64 | Hard | Arnaud Clement | 6-3 6-7(3) 2-6 1-4 (ret.) | L | H2H | Match data |
| Feb 10, 2000* | Dubai | ATP 250 | R32 | Hard | Oliver Gross | 6-3 6-2 | W | H2H | Match data |
| Feb 11, 2000* | Dubai | ATP 250 | R16 | Hard | Juan Carlos Ferrero | 4-6 3-6 | L | H2H | Match data |
| Feb 17, 2000* | Rotterdam | ATP 250 | R32 | Hard | Jonas Bjorkman | 6-7(5) 2-6 | L | H2H | Match data |
| Feb 24, 2000* | Mexico City | ATP 250 | R32 | Clay | Bohdan Ulihrach | 6-4 6-2 | W | H2H | Match data |