# Roger Federer's early career

Roger Federer's first ATP Tour-level tournament was the 1998 Gstaad Open, where he faced Lucas Arnold Ker in the round of 32 and lost, 4–6, 4–6. Federer's first final came at the 2000 Marseille Open, where he lost to fellow Swiss Marc Rosset, 6–2, 3–6, 6–7. Federer's first tournament win was at the 2001 Milan Indoor, where he defeated Julien Boutter, 6–4, 6–7, 6–4. The most prestigious finals he contested at this time included the 2002 Miami Masters, where he lost to Andre Agassi, 3–6, 3–6, 6–3, 4–6. Shortly thereafter, Federer won his first Masters Series event at the Hamburg Masters on clay, 6–1, 6–3, 6–4, over Marat Safin.
Federer made ten singles finals between 1998 and 2002, of which he won four and lost six. Federer made six doubles finals during this time, but lost the most prestigious of them at the 2002 Indian Wells Masters. The most prestigious events he won were the Hamburg Masters in 2002 and two Rotterdam 500 series events in 2001 and 2002.

## Yearly summary 1998–2002
### 1998: Joining the Tour

In July 1998, the 16-year-old Federer played his first ATP Tour event, the Swiss Open Gstaad, in his home country of Switzerland, losing to No. 88 Lucas Arnold Ker in the first round. Although he played two more ATP tournaments in 1998, the majority of his matches were still at the Junior level. Later that year, he won his first ATP match against Guillaume Raoux in Toulouse. He then received a wildcard into the 1998 Swiss Indoors in his hometown in Basel, where he used to be a ball boy. Having reached the quarterfinal in Toulouse a week earlier, Federer came to Basel as the world No. 396, but lost in the first round to former world No. 1 Andre Agassi. He finished 1998 ranked as the world No. 301.

### 1999: Grand Slam & Davis Cup debuts, Challenger titles, top 100

In February 1999, Federer reached the quarterfinal of ATP tournaments in Marseille and Rotterdam, defeating the reigning champion of the 1998 French Open, Carlos Moyá, in the former, to enter the Top 150 before the Miami Masters. His rise through the rankings was noticed by the Swiss Davis Cup captain Claudio Mezzadri, who invited him to join the squad for the World Group first round clash against Italy on home soil in Neuchatel. In April 1999, Federer made his Davis Cup debut against Italy, winning the rubber against No. 48 Davide Sanguinetti. In August, Federer won his first-ever professional title on the Challenger tour in Segovia, pairing with Sander Groen to beat Ota Fukárek and Alejandro Hernández in the final, which was played on Federer's 18th birthday.
He then competed in his first Grand Slam tournament at the French Open, but lost to Patrick Rafter in the first round after a four-set match. He also made his first appearance at Wimbledon, where he entered as a wildcard, but lost in the first round to No. 59 Jiří Novák in five sets. In the same tournament, Federer partnered Lleyton Hewitt in doubles, where they reached the round of 16, losing to Rafter and Jonas Björkman in another five-set match. Despite losing in the first rounds of both the French Open and Wimbledon and having just turned 18, he entered the world's Top 100 for the first time on 20 September 1999. At around that time, Federer was also a part of the Swiss military service, which was mandatory for all able-bodied male citizens when they reached the age of majority, and Federer was drafted in too. However, the then-18-year-old was discharged soon due to a chronic back problem.
In October 1999, Federer reached his first ATP semifinal in the Vienna Open, which he lost to Greg Rusedski. Later that month, Federer won his first and only singles ATP Challenger title in Brest, defeating Max Mirnyi in the final. In his first full year as a professional, Federer finished the year as the world No. 64, and in doing so at 18 years and four months of age, he became the youngest player to end the year among the world's top 100.

### 2000: First finals, Olympic 4th place, top 30

On 18 January 2000, the 18-year-old Federer played his first match in the main draw of the Australian Open, defeating former World No. 2 Michael Chang in the opening round to claim his first singles victory at a major event. However, he then lost to no. 49 Arnaud Clément in the third round. He equaled this achievement in his first US Open, losing in the third round to no. 12 Juan Carlos Ferrero. His first singles final came at the Marseille Open in February 2000, where he lost to fellow Swiss Marc Rosset. Federer then entered the Top 50 in March and ended 2000 ranked as the world No. 29. After reaching the semifinals at the 2000 Sydney Olympics, Federer was the runner-up in his home tournament at Basel. Even though he failed to make an impression at Grand Slams, it was the first year he played in all four. Federer then ended the year ranked world no. 29.

### 2001: Hopman Cup champion, first title, match with Sampras

Federer began the 2001 season by winning the 2001 Hopman Cup representing Switzerland, along with world No. 1 Martina Hingis. The duo defeated the American pair of Monica Seles and Jan-Michael Gambill in the finals. Federer later said that his experience with Hingis "definitely helped me to become the player I am today." In February 2001, Federer won his first ATP tournament after defeating Julien Boutter in the final of the Milan Indoor. During the same month, he won three matches for his country in its 3–2 Davis Cup victory over the United States in front of a home crowd in Basel, thus becoming only the fifth man in history to win every match against the United States, the most successful country in Davis Cup history with 31 titles. The last time a player defeated the United States in every match was in 1976. After a match against Marat Safin at the Rome Masters, in which both players threw their racquets several times, Federer decided to change his temper after watching himself in the highlight reel.
Federer reached his first Grand Slam quarterfinal at the French Open, losing to former world No. 2 and eventual finalist Àlex Corretja. His international breakthrough came at the Wimbledon Championships, when the 19-year-old Federer and the four-time defending champion and all-time Grand Slam leader Pete Sampras walked onto Centre Court for their only meeting in the fourth round. Federer, who was then ranked no. 15, defeated the No. 1 seed in a five-set match to snap Sampras' 31-match win streak at Wimbledon. The defeat was Sampras' first at the All England Club since 1996 and it ended his bid for a record-tying fifth consecutive title. In the quarters he faced Englishman Tim Henman, eventually losing in a fourth-set tiebreaker. Federer then had his best performance at the US Open by reaching the fourth round before falling to Andre Agassi. He finished 2001 with an ATP ranking of No. 13.

### 2002: Breakthrough and top 10, but Grand Slam struggles

Federer reached his first Masters Series final in 2002 at the 2002 Miami Masters event, where he lost to Andre Agassi. He won his next Masters final in Hamburg, defeating former world No. 1 Marat Safin. This was a major breakthrough for Federer as it was his first Masters championship and his most significant title at the time. He also won both his Davis Cup singles matches against former world No. 1 Russians Safin and Yevgeny Kafelnikov.
After early-round exits at the French Open and Wimbledon, Federer suffered the devastating loss of his long-time Australian coach and mentor, Peter Carter, in a car crash in August. Federer learned of Carter's death while competing at the Canadian Masters in Toronto and although he had already lost in the first round, Federer was still playing in the doubles tournament partnering with Wayne Ferreira, ironically, a South African. In the third round, which he and Ferreira lost to Joshua Eagle and Sandon Stolle, Federer played the match wearing a black armband in honor of Carter.
Although he suffered first-round losses in the three tournaments he entered after Carter's death, Federer gathered himself together and began playing with more determination than ever. After reaching the fourth round of the US Open, he showed greater consistency by winning the Vienna Open, beating Jiří Novák in the final to win his fourth title of the season, and then reaching the quarterfinals at Madrid and Paris to jump in the rankings from No. 13 at the end of September to No. 7 by early November. This qualified him for the first time for the year-end Tennis Masters Cup, where he won all of his matches in the round-robin stage with the loss of only one set before losing the semifinals to the then-world no. 1 and eventual champion Lleyton Hewitt. At age 21, he ended 2002 ranked as the world No. 6.

### Grand Slam performances

| Year | Tournament | Round | Result | Opponent | Score |
| 1999 | French Open | 1R | Loss | Patrick Rafter | 6–7, 6–3, 6–0, 6–2 |
| 1999 | Wimbledon | 1R | Loss | Jiří Novák | 6–3, 3–6, 4–6, 6–3, 6–4 |
| 2000 | Australian Open | 1R | Win | Michael Chang | 6–4, 6–4, 7–6$^{(7–5)}$ |
| 2000 | Australian Open | 2R | Win | Ján Krošlák | 7–6$^{(7–1)}$, 6–2, 6–3 |
| 2000 | Australian Open | 3R | Loss | Arnaud Clément | 6–1, 6–4, 6–3 |
| 2000 | French Open | 1R | Win | Wayne Arthurs | 7–6$^{(7–4)}$, 6–3, 1–6, 6–3 |
| 2000 | French Open | 2R | Win | Jan-Michael Gambill | 7–6$^{(7–5)}$, 6–3, 6–3 |
| 2000 | French Open | 3R | Win | Michel Kratochvil | 7–6$^{(7–5)}$, 6–4, 2–6, 6–7$^{(4–7)}$, 8–6 |
| 2000 | French Open | 4R | Loss | Àlex Corretja | 7–5, 7–6$^{(9–7)}$, 6–2 |
| 2000 | Wimbledon | 1R | Loss | Yevgeny Kafelnikov | 7–5, 7–5, 7–6$^{(8–6)}$ |
| 2000 | US Open | 1R | Win | Peter Wessels | 4–6, 4–6, 6–3, 7–5, 3–4 (ret.) |
| 2000 | US Open | 2R | Win | Daniel Nestor | 6–1, 7–6$^{(7–5)}$, 6–1 |
| 2000 | US Open | 3R | Loss | Juan Carlos Ferrero | 7–5, 7–6$^{(8–6)}$, 1–6, 7–6$^{(8–6)}$ |
| Year | Tournament | Round | Result | Opponent | Score |
| 2001 | Australian Open | 1R | Win | Arnaud Di Pasquale | 6–4, 4–6, 6–1, 6–4 |
| 2001 | Australian Open | 2R | Win | Nicolas Escudé | 6–1, 6–4, 6–4 |
| 2001 | Australian Open | 3R | Loss | Arnaud Clément | 7–6$^{(7–5)}$, 6–4, 6–4 |
| 2001 | French Open | 1R | Win | Stefano Galvani | 6–3, 6–3, 6–3 |
| 2001 | French Open | 2R | Win | Sargis Sargsian | 4–6, 3–6, 6–2, 6–4, 9–7 |
| 2001 | French Open | 3R | Win | David Sánchez | 6–4, 6–3, 1–6, 6–3 |
| 2001 | French Open | 4R | Win | Wayne Arthurs | 3–6, 6–3, 6–4, 6–2 |
| 2001 | French Open | QF | Loss | Àlex Corretja | 7–5, 6–4, 7–5 |
| 2001 | Wimbledon | 1R | Win | Olivier Rochus | 6–2, 6–3, 6–2 |
| 2001 | Wimbledon | 2R | Win | Xavier Malisse | 6–3, 7–5, 3–6, 4–6, 6–3 |
| 2001 | Wimbledon | 3R | Win | Jonas Björkman | 7–6$^{(7–4)}$, 6–3, 7–6$^{(7–2)}$ |
| 2001 | Wimbledon | 4R | Win | Pete Sampras | 7–6$^{(9–7)}$, 5–7, 6–4, 6–7$^{(2–7)}$, 7–5 |
| 2001 | Wimbledon | QF | Loss | Tim Henman | 7–5, 7–6$^{(8–6)}$, 2–6, 7–6$^{(8–6)}$ |
| 2001 | US Open | 1R | Win | Lars Burgsmüller | 6–4, 6–4, 6–4 |
| 2001 | US Open | 2R | Win | Robby Ginepri | 6–2, 7–5, 6–1 |
| 2001 | US Open | 3R | Win | Sjeng Schalken | 6–4, 7–5, 7–6$^{(7–3)}$ |
| 2001 | US Open | 4R | Loss | Andre Agassi | 6–1, 6–2, 6–4 |
| 2002 | Australian Open | 1R | Win | Michael Chang | 6–4, 6–4, 6–3 |
| 2002 | Australian Open | 2R | Win | Attila Sávolt | 6–2, 7–5, 6–4 |
| 2002 | Australian Open | 3R | Win | Rainer Schüttler | 7–6$^{(8–6)}$, 7–6$^{(7–5)}$, 6–4 |
| 2002 | Australian Open | 4R | Loss | Tommy Haas | 7–6$^{(7–3)}$, 4–6, 3–6, 6–4, 8–6 |
| 2002 | French Open | 1R | Loss | Hicham Arazi | 6–3, 6–2, 6–4 |
| 2002 | Wimbledon | 1R | Loss | Mario Ančić | 6–3, 7–6$^{(7–2)}$, 6–3 |
| 2002 | US Open | 1R | Win | Jiří Vaněk | 6–1, 6–3, 4–6, 7–5 |
| 2002 | US Open | 2R | Win | Michael Chang | 6–3, 6–1, 6–3 |
| 2002 | US Open | 3R | Win | Xavier Malisse | 4–6, 6–3, 6–4, 6–4 |
| 2002 | US Open | 4R | Loss | Max Mirnyi | 6–3, 7–6$^{(7–5)}$, 6–4 |

### All Matches in Singles
#### 1998

| Tournament | Match | Round | Opponent (seed or key) | Rank | Result | Score |
| Rado Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 6 – 12 July 1998 |
| Rado Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 6 – 12 July 1998 | 1 | 1R | Lucas Arnold Ker (LL) | 88 | Loss | 4–6, 4–6 |
| Geneva Open Challenger Geneva, Switzerland ATP Challenger Tour Clay, outdoor 24 – 30 August 1998 |
| Geneva Open Challenger Geneva, Switzerland ATP Challenger Tour Clay, outdoor 24 – 30 August 1998 | – | 1R | Orlin Stanoytchev (5) | 124 | Loss | 4–6, 6–7 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | – | Q1 | Marcello Wowk | 672 | Win | 7–6, 6–2 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | – | Q2 | Alex Rădulescu (3) | 160 | Win | 7–6, 7–6 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | – | Q3 | Olivier Delaître (6) | 215 | Win | 6–4, 6–4 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | 2 | 1R | Guillaume Raoux | 45 | Win | 6–2, 6–2 |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | 3 | 2R | Richard Fromberg (7) | 43 | Win | 6–1, 7–6$^{(7–5)}$ |
| Grand Prix de Tennis de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 28 September – 4 October 1998 | 4 | QF | Jan Siemerink (2) | 20 | Loss | 6–7$^{(5–7)}$, 2–6 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Hard, indoor 5 – 11 October 1998 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Hard, indoor 5 – 11 October 1998 | 5 | 1R | Andre Agassi (4) | 8 | Loss | 3–6, 2–6 |

#### 1999

| Tournament | Match | Round | Opponent (seed or key) | Rank | Result | Score |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 18 – 31 January 1999 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 18 – 31 January 1999 | – | Q1 | Olivier Delaître | 193 | Loss | 4–6, 4–6 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | Q1 | Raemon Sluiter | 250 | Win | 6–2, 6–4 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | Q2 | Radek Štěpánek (4) | 168 | Win | 6–4, 6–1 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | Q3 | Stefano Pescosolido (6) | 182 | Win | 6–1, 6–1 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | 1R | Cristiano Caratti (Q) | 161 | Win | 7–5, 6–4 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | 2R | John van Lottum (6) | 100 | Win | 6–2, 6–4 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | QF | Justin Gimelstob (3) | 80 | Win | 6–7, 7–6, 7–5 |
| Intersport Heilbronn Open Talheim, Germany ATP Challenger Tour Carpet, indoor 25 – 31 January 1999 | – | SF | Laurence Tieleman (7) | 106 | Loss | 5–7, 1–6 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 1 – 8 February 1999 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 1 – 8 February 1999 | 6 | 1R | Carlos Moyá (1) | 5 | Win | 7–6$^{(7–1)}$, 3–6, 6–3 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 1 – 8 February 1999 | 7 | 2R | Jérôme Golmard | 63 | Win | 6–7$^{(6–8)}$, 7–6$^{(7–5)}$, 7–6$^{(7–5)}$ |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 1 – 8 February 1999 | 8 | QF | Arnaud Clément (WC) | 103 | Loss | 3–6, 3–6 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 | – | Q1 | Hendrik Dreekmann (6) | 89 | Walkover | N/A |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 | – | Q2 | Martin Damm (3) | 72 | Win | 6–2, 7–6 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 | 9 | 1R | Guillaume Raoux | 71 | Win | 6–7$^{(4–7)}$, 7–5, 7–6$^{(7–3)}$ |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 | 10 | 2R | Bohdan Ulihrach | 30 | Win | 6–4, 7–5 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Carpet, indoor 15 – 21 February 1999 | 11 | QF | Yevgeny Kafelnikov (2) | 2 | Loss | 1–6, 7–5, 4–6 |
| Grenoble Challenger Grenoble, France ATP Challenger Tour Hard, indoor 1 – 7 March 1999 |
| Grenoble Challenger Grenoble, France ATP Challenger Tour Hard, indoor 1 – 7 March 1999 | – | 1R | Rodolphe Gilbert | 191 | Win | 6–2, 6–0 |
| Grenoble Challenger Grenoble, France ATP Challenger Tour Hard, indoor 1 – 7 March 1999 | – | 2R | Julien Boutter (Q) | 215 | Loss | 6–4, 2–6, 3–6 |
| Lipton Championships Miami, United States ATP Tour Masters 1000 Hard, outdoor 15 – 29 March 1999 |
| Lipton Championships Miami, United States ATP Tour Masters 1000 Hard, outdoor 15 – 29 March 1999 | 12 | 1R | Kenneth Carlsen | 106 | Loss | 5–7, 6–7$^{(4–7)}$ |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 2 – 4 April 1999 |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 2 – 4 April 1999 | 13 | 1R R2 | Davide Sanguinetti | 48 | Win | 6–4, 6–7$^{(3–7)}$, 6–3, 6–4 |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 2 – 4 April 1999 | 14 | 1R R5 | Gianluca Pozzi | 69 | Loss | 4–6, 6–7$^{(4–7)}$ |
| Monte Carlo Open Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 19 – 25 April 1999 |
| Monte Carlo Open Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 19 – 25 April 1999 | 15 | 1R | Vincent Spadea | 33 | Loss | 6–7$^{(3–7)}$, 0–6 |
| Espinho Challenger Espinho, Portugal ATP Challenger Tour Clay, outdoor 26 April – 2 May 1999 |
| Espinho Challenger Espinho, Portugal ATP Challenger Tour Clay, outdoor 26 April – 2 May 1999 | – | 1R | Joan Balcells (Q) | 291 | Loss | 6–7, 3–6 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | Q1 | Igor Ogrinc | – | Win | 6–3, 7–5 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | Q2 | Blaž Trupej | 605 | Win | 6–3, 6–7, 6–3 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | Q3 | David Sánchez (8) | 253 | Win | 6–2, 7–5 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | 1R | Eduardo Medica (5) | 117 | Win | 6–3, 6–2 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | 2R | Radomír Vašek (Q) | 237 | Win | 7–6, 6–1 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | QF | Juan Albert Viloca | 149 | Win | 2–6, 6–3, 6–4 |
| Renault Slovenian Open Domžale, Slovenia ATP Challenger Tour Clay, outdoor 3 – 9 May 1999 | – | SF | Dinu Pescariu (1) | 99 | Loss | 6–7, 2–6 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 24 May – 6 June 1999 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 24 May – 6 June 1999 | 16 | 1R | Patrick Rafter (3) | 3 | Loss | 7–5, 3–6, 0–6, 2–6 |
| Surbiton Trophy Surbiton, United Kingdom ATP Challenger Tour Grass, outdoor 31 May – 6 June 1999 |
| Surbiton Trophy Surbiton, United Kingdom ATP Challenger Tour Grass, outdoor 31 May – 6 June 1999 | – | 1R | Maurice Ruah | 175 | Win | 7–6, 6–2 |
| Surbiton Trophy Surbiton, United Kingdom ATP Challenger Tour Grass, outdoor 31 May – 6 June 1999 | – | 2R | John van Lottum (2) | 64 | Win | 6–3, 3–6, 6–1 |
| Surbiton Trophy Surbiton, United Kingdom ATP Challenger Tour Grass, outdoor 31 May – 6 June 1999 | – | QF | Alex O'Brien | 173 | Win | 6–1, 6–4 |
| Surbiton Trophy Surbiton, United Kingdom ATP Challenger Tour Grass, outdoor 31 May – 6 June 1999 | – | SF | Sargis Sargsian (5) | 75 | Loss | 7–6, 3–6, 6–7 |
| Stella Artois Championships London, United Kingdom ATP Tour 250 Grass, outdoor 7 – 13 June 1999 |
| Stella Artois Championships London, United Kingdom ATP Tour 250 Grass, outdoor 7 – 13 June 1999 | 17 | 1R | Byron Black (13) | 37 | Loss | 3–6, 0–6 |
| Nottingham Open Nottingham, United Kingdom ATP Tour 250 Grass, outdoor 14 – 20 June 1999 |
| Nottingham Open Nottingham, United Kingdom ATP Tour 250 Grass, outdoor 14 – 20 June 1999 | – | Q1 | Ben Haran | – | Win | 6–1, 6–1 |
| Nottingham Open Nottingham, United Kingdom ATP Tour 250 Grass, outdoor 14 – 20 June 1999 | – | Q2 | Donald Johnson | 581 | Loss | 3–6, 2–6 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 21 June – 4 July 1999 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 21 June – 4 July 1999 | 18 | 1R | Jiří Novák | 59 | Loss | 3–6, 6–3, 6–4, 3–6, 4–6 |
| Rado Swiss Open Gstaad Gstaad, Switzerland ATP Tour 250 Clay, outdoor 5 – 11 July 1999 |
| Rado Swiss Open Gstaad Gstaad, Switzerland ATP Tour 250 Clay, outdoor 5 – 11 July 1999 | 19 | 1R | Younes El Aynaoui | 33 | Loss | 2–6, 3–6 |
| Davis Cup, World Group Brussels, Belgium Davis Cup Clay, outdoor 16 – 18 July 1999 |
| Davis Cup, World Group Brussels, Belgium Davis Cup Clay, outdoor 16 – 18 July 1999 | 20 | QF R2 | Christophe Van Garsse | 146 | Loss | 6–7$^{(4–7)}$, 6–3, 6–1, 5–7, 1–6 |
| Davis Cup, World Group Brussels, Belgium Davis Cup Clay, outdoor 16 – 18 July 1999 | 21 | QF R4 | Xavier Malisse | 111 | Loss | 6–4, 3–6, 5–7, 6–7$^{(5–7)}$ |
| Open Castilla y León Segovia, Spain ATP Challenger Tour Clay, outdoor 2 – 8 August 1999 |
| Open Castilla y León Segovia, Spain ATP Challenger Tour Clay, outdoor 2 – 8 August 1999 | – | 1R | Quino Muñoz (WC) | 520 | Win | 7–6$^{(7–5)}$, 6–4 |
| Open Castilla y León Segovia, Spain ATP Challenger Tour Clay, outdoor 2 – 8 August 1999 | – | 2R | Nicolas Escudé | 139 | Loss | 6–3, 1–6, 4–6 |
| Legg Mason Tennis Classic Washington, D.C., United States ATP Tour 500 Hard, outdoor 16 – 22 August 1999 |
| Legg Mason Tennis Classic Washington, D.C., United States ATP Tour 500 Hard, outdoor 16 – 22 August 1999 | 22 | 1R | Bjorn Phau (Q) | 407 | Loss | 2–6, 3–6 |
| Waldbaum's Hamlet Cup Long Island, United States ATP Tour 250 Hard, outdoor 23 – 29 August 1999 |
| Waldbaum's Hamlet Cup Long Island, United States ATP Tour 250 Hard, outdoor 23 – 29 August 1999 | – | Q1 | Todd Meringoff (WC) | 796 | Win | 6–2, 3–6, 6–3 |
| Waldbaum's Hamlet Cup Long Island, United States ATP Tour 250 Hard, outdoor 23 – 29 August 1999 | – | Q2 | Eric Taino (WC) | 504 | Loss | 2–6, 2–6 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 30 August – 12 September 1999 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 30 August – 12 September 1999 | – | Q1 | Edwin Kempes | 228 | Win | 6–4, 6–4 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 30 August – 12 September 1999 | – | Q2 | Ivo Heuberger | 231 | Loss | 6–7, 2–6 |
| President's Cup Tashkent, Uzbekistan ATP Tour 250 Hard, outdoor 13 – 19 September 1999 |
| President's Cup Tashkent, Uzbekistan ATP Tour 250 Hard, outdoor 13 – 19 September 1999 | 23 | 1R | Cédric Pioline (5) | 16 | Win | 6–4, 6–3 |
| President's Cup Tashkent, Uzbekistan ATP Tour 250 Hard, outdoor 13 – 19 September 1999 | 24 | 2R | Peter Wessels | 92 | Loss | 6–4, 6–7$^{(1–7)}$, 4–6 |
| Adidas Open de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 27 September – 3 October 1999 |
| Adidas Open de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 27 September – 3 October 1999 | 25 | 1R | Rainer Schüttler | 46 | Win | 7–6$^{(7–4)}$, 6–1 |
| Adidas Open de Toulouse Toulouse, France ATP Tour 250 Hard, indoor 27 September – 3 October 1999 | 26 | 2R | Fabrice Santoro (7) | 39 | Loss | 3–6, 6–7$^{(3–7)}$ |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 3 – 10 October 1999 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 3 – 10 October 1999 | 27 | 1R | Martin Damm (LL) | 105 | Win | 6–2, 3–6, 6–4 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 3 – 10 October 1999 | 28 | 2R | Alexander Popp (Q) | 134 | Win | 6–2, 7–5 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 3 – 10 October 1999 | 29 | QF | Tim Henman (4) | 6 | Loss | 3–6, 5–7 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Carpet, indoor 11 – 18 October 1999 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Carpet, indoor 11 – 18 October 1999 | 30 | 1R | Vince Spadea | 21 | Win | 6–4, 6–2 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Carpet, indoor 11 – 18 October 1999 | 31 | 2R | Jiří Novák | 34 | Win | 7–6$^{(10–8)}$, 6–1 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Carpet, indoor 11 – 18 October 1999 | 32 | QF | Karol Kučera | 15 | Win | 2–6, 6–4, 6–1 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Carpet, indoor 11 – 18 October 1999 | 33 | SF | Greg Rusedski (5) | 7 | Loss | 3–6, 4–6 |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 18 – 25 October 1999 |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 18 – 25 October 1999 | 34 | 1R | Daniel Vacek | 53 | Win | 6–3, 6–4 |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 18 – 25 October 1999 | 35 | 2R | Lleyton Hewitt (13) | 27 | Win | 6–7$^{(4–7)}$, 6–2, 4–6 |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 | – | 1R | Lionel Roux (WC) | 191 | Win | 6–3, 4–6, 6–4 |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 | – | 2R | Rodolphe Gilbert | 180 | Win | 6–4, 6–3 |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 | – | QF | Michaël Llodra (WC) | 333 | Win | 6–3, 6–3 |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 | – | SF | Martin Damm | 134 | Win | 6–3, 7–6$^{(7–4)}$ |
| Brest Challenger Brest, France ATP Challenger Tour Hard, indoor 25 – 31 October 1999 | – | W | Max Mirnyi (5) | 90 | Win | 7–6$^{(7–4)}$, 6–3 |
| Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 8 – 14 November 1999 |
| Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 8 – 14 November 1999 | – | Q1 | Cristiano Caratti | 218 | Win | 6–3, 7–5 |
| Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 8 – 14 November 1999 | – | Q2 | Marcus Sarstrand | 447 | Loss | 2–6, 6–4, 6–7 |

#### 2000

| Tournament | Match | Round | Opponent (seed or key) | Rank | Result | Score |
| AAPT Championships Adelaide, Australia ATP Tour 250 Hard, outdoor 3 – 9 January 2000 |
| AAPT Championships Adelaide, Australia ATP Tour 250 Hard, outdoor 3 – 9 January 2000 | 36 | 1R | Jens Knippschild | 91 | Win | 6–1, 6–4 |
| AAPT Championships Adelaide, Australia ATP Tour 250 Hard, outdoor 3 – 9 January 2000 | 37 | 2R | Thomas Enqvist (1) | 4 | Loss | 6–7$^{(5–7)}$, 4–6 |
| Heineken Open Auckland, New Zealand ATP Tour 250 Hard, outdoor 10 – 15 January 2000 |
| Heineken Open Auckland, New Zealand ATP Tour 250 Hard, outdoor 10 – 15 January 2000 | 38 | 1R | Juan Carlos Ferrero (7) | 45 | Loss | 4–6, 4–6 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 17 – 30 January 2000 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 17 – 30 January 2000 | 39 | 1R | Michael Chang | 38 | Win | 6–4, 6–4, 7–6$^{(7–5)}$ |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 17 – 30 January 2000 | 40 | 2R | Ján Krošlák | 104 | Win | 7–6$^{(7–1)}$, 6–2, 6–3 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 17 – 30 January 2000 | 41 | 3R | Arnaud Clément | 54 | Loss | 1–6, 4–6, 3–6 |
| Davis Cup, World Group Zürich, Switzerland Davis Cup Carpet, indoor 4 – 6 February 2000 |
| Davis Cup, World Group Zürich, Switzerland Davis Cup Carpet, indoor 4 – 6 February 2000 | 42 | 1R R2 | Mark Philippoussis | 17 | Win | 6–4, 7–6$^{(7–3)}$, 4–6, 6–4 |
| Davis Cup, World Group Zürich, Switzerland Davis Cup Carpet, indoor 4 – 6 February 2000 | 43 | 1R R4 | Lleyton Hewitt | 15 | Loss | 2–6, 6–3, 6–7$^{(2–7)}$, 1–6 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 | 44 | 1R | Antony Dupuis (Q) | 93 | Win | 6–4, 6–4 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 | 45 | 2R | Thomas Johansson (7) | 41 | Win | 6–3, 6–2 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 | 46 | QF | Ivan Ljubičić | 69 | Win | 6–2, 3–6, 7–6$^{(7–5)}$ |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 | 47 | SF | Fabrice Santoro (6) | 38 | Win | 7–6$^{(7–4)}$, 7–5 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 7 – 14 February 2000 | 48 | F | Marc Rosset | 77 | Loss (1) | 6–2, 3–6, 6–7$^{(5–7)}$ |
| AXA Cup London, United Kingdom ATP Tour 500 Hard, indoor 21 – 27 February 2000 |
| AXA Cup London, United Kingdom ATP Tour 500 Hard, indoor 21 – 27 February 2000 | 49 | 1R | Nicolas Kiefer (2) | 4 | Win | 6–2, 6–3 |
| AXA Cup London, United Kingdom ATP Tour 500 Hard, indoor 21 – 27 February 2000 | 50 | 2R | Goran Ivanišević (WC) | 61 | Win | 7–5, 6–3 |
| AXA Cup London, United Kingdom ATP Tour 500 Hard, indoor 21 – 27 February 2000 | 51 | QF | Marc Rosset | 72 | Loss | 6–3, 4–6, 4–6 |
| Copenhagen Open Copenhagen, Denmark ATP Tour 250 Hard, indoor 26 February – 5 March 2000 |
| Copenhagen Open Copenhagen, Denmark ATP Tour 250 Hard, indoor 26 February – 5 March 2000 | 52 | 1R | Filip Dewulf (Q) | 234 | Win | 6–4, 4–6, 6–3 |
| Copenhagen Open Copenhagen, Denmark ATP Tour 250 Hard, indoor 26 February – 5 March 2000 | 53 | 2R | Fredrik Jonsson | 121 | Win | 6–4, 6–4 |
| Copenhagen Open Copenhagen, Denmark ATP Tour 250 Hard, indoor 26 February – 5 March 2000 | 54 | QF | Gianluca Pozzi | 83 | Win | 4–6, 6–1, 6–3 |
| Copenhagen Open Copenhagen, Denmark ATP Tour 250 Hard, indoor 26 February – 5 March 2000 | 55 | SF | Magnus Larsson (3) | 48 | Loss | 3–6, 6–7$^{(6–8)}$ |
| Indian Wells Masters Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 10 – 18 March 2000 |
| Indian Wells Masters Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 10 – 18 March 2000 | – | Q1 | Leander Paes | 117 | Loss | 7–5, 1–6, 4–6 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 23 March – 2 April 2000 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 23 March – 2 April 2000 | 56 | 1R | Justin Gimelstob (WC) | 99 | Win | 7–5, 6–3 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 23 March – 2 April 2000 | 57 | 2R | Mariano Zabaleta (23) | 25 | Loss | 4–6, 6–7$^{(7–9)}$ |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 17 – 23 April 2000 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 17 – 23 April 2000 | 58 | 1R | Jiří Novák | 37 | Loss | 1–6, 6–2, 5–7 |
| Torneo Godó Barcelona, Spain ATP Tour 500 Clay, outdoor 24 – 30 April 2000 |
| Torneo Godó Barcelona, Spain ATP Tour 500 Clay, outdoor 24 – 30 April 2000 | 59 | 1R | Sergi Bruguera (WC) | 249 | Loss | 1–6, 1–6 |
| Italian Open Rome, Italy ATP Tour Masters 1000 Clay, outdoor 8 – 14 May 2000 |
| Italian Open Rome, Italy ATP Tour Masters 1000 Clay, outdoor 8 – 14 May 2000 | 60 | 1R | Andrei Medvedev | 25 | Loss | 6–3, 3–6, 5–7 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 15 – 21 May 2000 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 15 – 21 May 2000 | 61 | 1R | Andrei Pavel (Q) | 70 | Loss | 4–6, 3–6 |
| International Raiffeisen Grand Prix Sankt Pölten, Austria ATP Tour 250 Clay, outdoor 22 – 28 May 2000 |
| International Raiffeisen Grand Prix Sankt Pölten, Austria ATP Tour 250 Clay, outdoor 22 – 28 May 2000 | 62 | 1R | Markus Hantschk | 94 | Loss | 2–6, 1–6 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 22 – 28 May 2000 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 22 – 28 May 2000 | 63 | 1R | Wayne Arthurs | 106 | Win | 7–6$^{(7–4)}$, 6–3, 1–6, 6–3 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 22 – 28 May 2000 | 64 | 2R | Jan-Michael Gambill | 69 | Win | 7–6$^{(7–5)}$, 6–3, 6–3 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 22 – 28 May 2000 | 65 | 3R | Michel Kratochvil (Q) | 120 | Win | 7–6$^{(7–5)}$, 6–4, 2–6, 6–7$^{(4–7)}$, 8–6 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 22 – 28 May 2000 | 66 | 4R | Àlex Corretja (10) | 10 | Loss | 5–7, 6–7$^{(7–9)}$, 2–6 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 12 – 18 June 2000 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 12 – 18 June 2000 | 67 | 1R | Arnaud Clément | 57 | Win | 6–4, 6–2 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 12 – 18 June 2000 | 68 | 2R | Magnus Larsson | 49 | Win | 6–2, 6–3 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 12 – 18 June 2000 | 69 | QF | Michael Chang | 28 | Loss | 5–7, 2–6 |
| Nottingham Open Nottingham, United Kingdom ATP Tour 250 Grass, outdoor 19 – 25 June 2000 |
| Nottingham Open Nottingham, United Kingdom ATP Tour 250 Grass, outdoor 19 – 25 June 2000 | 70 | 1R | Richard Fromberg | 71 | Loss | 5–7, 1–6 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 26 June – 9 July 2000 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 26 June – 9 July 2000 | 71 | 1R | Yevgeny Kafelnikov (5) | 5 | Loss | 5–7, 5–7, 6–7$^{(6–8)}$ |
| UBS Open Gstaad Gstaad, Switzerland ATP Tour 250 Clay, outdoor 10 – 17 July 2000 |
| UBS Open Gstaad Gstaad, Switzerland ATP Tour 250 Clay, outdoor 10 – 17 July 2000 | 72 | 1R | Àlex Corretja (1) | 10 | Loss | 4–6, 6–4, 4–6 |
| Davis Cup, World Group Play-offs St. Gallen, Switzerland Davis Cup Carpet, indoor 21 – 23 July 2000 |
| Davis Cup, World Group Play-offs St. Gallen, Switzerland Davis Cup Carpet, indoor 21 – 23 July 2000 | 73 | PO R2 | Vladimir Voltchkov | 69 | Win | 4–6, 7–5, 7–6$^{(7–1)}$, 5–7, 6–2 |
| du Maurier Open Toronto, Canada ATP Tour Masters 1000 Hard, outdoor 31 July – 6 August 2000 |
| du Maurier Open Toronto, Canada ATP Tour Masters 1000 Hard, outdoor 31 July – 6 August 2000 | 74 | 1R | Lleyton Hewitt (7) | 10 | Loss | 6–3, 3–6, 2–6 |
| Cincinnati Masters Cincinnati, United States ATP Tour Masters 1000 Hard, outdoor 7 – 14 August 2000 |
| Cincinnati Masters Cincinnati, United States ATP Tour Masters 1000 Hard, outdoor 7 – 14 August 2000 | 75 | 1R | Francisco Clavet | 43 | Loss | 6–7$^{(3–7)}$, 6–7$^{(4–7)}$ |
| RCA Championships Indianapolis, United States ATP Tour 500 Hard, outdoor 14 – 20 August 2000 |
| RCA Championships Indianapolis, United States ATP Tour 500 Hard, outdoor 14 – 20 August 2000 | 76 | 1R | James Sekulov | 191 | Loss | 4–6, 5–7 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 28 August – 10 September 2000 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 28 August – 10 September 2000 | 77 | 1R | Peter Wessels | 89 | Win | 4–6, 4–6, 6–3, 7–5, 3–4, ret. |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 28 August – 10 September 2000 | 78 | 2R | Daniel Nestor (PR) | 307 | Win | 6–1, 7–6$^{(7–5)}$, 6–1 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 28 August – 10 September 2000 | 79 | 3R | Juan Carlos Ferrero (12) | 12 | Loss | 5–7, 6–7$^{(6–8)}$, 6–1, 6–7$^{(6–8)}$ |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 80 | 1R | David Prinosil | 60 | Win | 6–2, 6–2 |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 81 | 2R | Karol Kučera | 43 | Win | 6–4, 7–6$^{(7–5)}$ |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 82 | 3R | Mikael Tillström (Alt) | 61 | Win | 6–1, 6–2 |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 83 | QF | Karim Alami | 34 | Win | 7–6$^{(7–2)}$, 6–1 |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 84 | SF | Tommy Haas | 48 | Loss | 3–6, 2–6 |
| Summer Olympics Sydney, Australia Olympic Games Hard, outdoor 19 – 28 September 2000 | 85 | SF-B | Arnaud Di Pasquale | 62 | Loss | 6–7$^{(5–7)}$, 7–6$^{(9–7)}$, 3–6 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 9 – 15 October 2000 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 9 – 15 October 2000 | 86 | 1R | Magnus Norman (2) | 4 | Win | 4–6, 7–6$^{(7–4)}$, 6–4 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 9 – 15 October 2000 | 87 | 2R | Max Mirnyi (Q) | 43 | Win | 6–3, 6–3 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 9 – 15 October 2000 | 88 | QF | Richard Krajicek | 20 | Win | 6–4, 6–3 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 9 – 15 October 2000 | 89 | SF | Tim Henman (6) | 10 | Loss | 6–2, 6–7$^{(4–7)}$, 3–6 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 | 90 | 1R | Tommy Haas (WC) | 20 | Win | 6–3, 6–3 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 | 91 | 2R | Andrei Pavel | 27 | Win | 7–6$^{(7–4)}$, 6–4 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 | 92 | QF | Nicolas Thomann (Q) | 185 | Win | 6–4, 6–4 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 | 93 | SF | Lleyton Hewitt (3) | 9 | Win | 6–4, 5–7, 7–6$^{(8–6)}$ |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet, indoor 24 – 29 October 2000 | 94 | F | Thomas Enqvist (2) | 6 | Loss (2) | 2–6, 6–4, 6–7$^{(4–7)}$, 6–1, 1–6 |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 30 October – 6 November 2000 |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 30 October – 6 November 2000 | 95 | 1R | Jan-Michael Gambill | 27 | Win | 7–6$^{(7–3)}$, 1–0, retired |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 30 October – 6 November 2000 | 96 | 2R | Yevgeny Kafelnikov (6) | 5 | Loss | 5–7, 3–6 |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 6 – 13 November 2000 |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 6 – 13 November 2000 | 97 | 1R | Nicolas Escudé | 38 | Win | 6–3, 7–6$^{(7–3)}$ |
| Grand Prix de Tennis de Lyon Lyon, France ATP Tour 250 Carpet, indoor 6 – 13 November 2000 | 98 | 2R | Karol Kučera | 74 | Loss | 6–3, 2–6, 1–6 |
| Paris Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 13 – 20 November 2000 |
| Paris Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 13 – 20 November 2000 | 99 | 1R | Dominik Hrbatý | 19 | Loss | 6–4, 2–6, 2–6 |
| Scania Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 20 – 26 November 2000 |
| Scania Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 20 – 26 November 2000 | 100 | 1R | Mikhail Youzhny | 110 | Win | 5–7, 6–4, 6–3 |
| Scania Stockholm Open Stockholm, Sweden ATP Tour 250 Hard, indoor 20 – 26 November 2000 | 101 | 2R | Andreas Vinciguerra | 55 | Loss | 5–7, 6–7$^{(3–7)}$ |

#### 2001

| Tournament | Match | Round | Opponent (seed or key) | Rank | Result | Score |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 7 – 14 January 2001 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 7 – 14 January 2001 | 102 | 1R | Wayne Ferreira (3) | 13 | Win | 6–3, 6–4 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 7 – 14 January 2001 | 103 | 2R | Marc Rosset | 29 | Win | 6–1, 6–2 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 7 – 14 January 2001 | 104 | QF | Sébastien Grosjean (6) | 19 | Loss | 5–7, 4–6 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 15 – 28 January 2001 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 15 – 28 January 2001 | 105 | 1R | Arnaud Di Pasquale | 61 | Win | 6–4, 4–6, 6–1, 7–5 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 15 – 28 January 2001 | 106 | 2R | Nicolas Escudé | 46 | Win | 6–1, 6–4, 6–4 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 15 – 28 January 2001 | 107 | 3R | Arnaud Clément (15) | 18 | Loss | 6–7$^{(5–7)}$, 4–6, 4–6 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 | 108 | 1R | Rainer Schüttler | 48 | Win | 6–3, 6–4 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 | 109 | 2R | Cyril Saulnier (Q) | 120 | Win | 2–6, 6–3, 6–4 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 | 110 | QF | Goran Ivanišević (WC) | 123 | Win | 6–4, 6–4 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 | 111 | SF | Yevgeny Kafelnikov (2) | 7 | Win | 6–2, 6–7$^{(4–7)}$, 6–3 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 29 January – 4 February 2001 | 112 | W | Julien Boutter | 67 | Win (1) | 6–4, 6–7$^{(7–9)}$, 6–4 |
| Davis Cup, World Group Basel, Switzerland Davis Cup Hard, indoor 9 – 11 February 2001 |
| Davis Cup, World Group Basel, Switzerland Davis Cup Hard, indoor 9 – 11 February 2001 | 113 | 1R R1 | Todd Martin | 37 | Win | 6–4, 7–6$^{(7–3)}$, 4–6, 6–1 |
| Davis Cup, World Group Basel, Switzerland Davis Cup Hard, indoor 9 – 11 February 2001 | 114 | 1R R4 | Jan-Michael Gambill | 28 | Win | 7–5, 6–2, 4–6, 6–2 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 12 – 19 February 2001 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 12 – 19 February 2001 | 115 | 1R | Cyril Saulnier (WC) | 114 | Win | 7–6$^{(9–7)}$, 6–4 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 12 – 19 February 2001 | 116 | 2R | Bob Bryan (Q) | 146 | Win | 7–6$^{(7–1)}$, 6–3 |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 12 – 19 February 2001 | 117 | QF | Michel Kratochvil | 78 | Win | 6–4, 7–6$^{(7–4)}$ |
| Open 13 Marseille, France ATP Tour 250 Hard, indoor 12 – 19 February 2001 | 118 | SF | Yevgeny Kafelnikov (2) | 7 | Loss | 7–6$^{(7–4)}$, 4–6, 4–6 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 | 119 | 1R | Andrew Ilie | 42 | Win | 7–6$^{(7–5)}$, 6–1 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 | 120 | 2R | Sébastien Grosjean (7) | 13 | Win | 4–6, 6–3, 6–4 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 | 121 | QF | Àlex Corretja (3) | 8 | Win | 6–4, 6–2 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 | 122 | SF | Andrei Pavel | 24 | Win | 6–7$^{(4–7)}$, 6–4, 6–0 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 19 – 25 February 2001 | 123 | F | Nicolas Escudé (Q) | 60 | Loss (3) | 5–7, 6–3, 6–7$^{(5–7)}$ |
| Indian Wells Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 8 – 18 March 2001 |
| Indian Wells Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 8 – 18 March 2001 | 124 | 1R | Nicolas Kiefer | 43 | Loss | 6–3, 5–7, 1–6 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 | – | 1R | Bye | Bye | Bye | Bye |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 | 125 | 2R | Younes El Aynaoui | 58 | Win | 6–2, 6–2 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 | 126 | 3R | Mark Philippoussis (16) | 16 | Win | 3–6, 7–6$^{(7–4)}$, 6–2 |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 | 127 | 4R | Thomas Johansson (25) | 25 | Win | 7–6$^{(7–3)}$, 5–7, 7–6$^{(9–7)}$ |
| Ericsson Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 21 March – 1 April 2001 | 128 | QF | Patrick Rafter (8) | 8 | Loss | 3–6, 1–6 |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 6 – 8 April 2001 |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 6 – 8 April 2001 | 129 | QF R2 | Nicolas Escudé | 34 | Loss | 4–6, 7–6$^{(7–1)}$, 3–6, 4–6 |
| Davis Cup, World Group Neuchâtel, Switzerland Davis Cup Carpet, indoor 6 – 8 April 2001 | 130 | QF R4 | Arnaud Clément | 10 | Win | 6–4, 3–6, 7–6$^{(7–5)}$, 6–4 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 16 – 22 April 2001 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 16 – 22 April 2001 | 131 | 1R | Michael Chang | 33 | Win | 6–4, 6–3 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 16 – 22 April 2001 | 132 | 2R | Davide Sanguinetti | 55 | Win | 7–6$^{(7–5)}$, 7–6$^{(7–0)}$ |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 16 – 22 April 2001 | 133 | 3R | Arnaud Di Pasquale | 67 | Win | 6–1, 6–2 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 16 – 22 April 2001 | 134 | QF | Sébastien Grosjean (9) | 15 | Loss | 4–6, 3–6 |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 7 – 13 May 2001 |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 7 – 13 May 2001 | 135 | 1R | Thomas Johansson | 24 | Win | 7–6$^{(7–3)}$, 4–6, 7–6$^{(7–5)}$ |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 7 – 13 May 2001 | 136 | 2R | Marat Safin (2) | 2 | Win | 4–6, 6–4, 7–6$^{(7–5)}$ |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 7 – 13 May 2001 | 137 | 3R | Wayne Ferreira | 19 | Loss | 6–7$^{(4–7)}$, 2–6 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 14 – 20 May 2001 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 14 – 20 May 2001 | 138 | 1R | Franco Squillari | 19 | Loss | 3–6, 4–6 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 | 139 | 1R | Stefano Galvani (Q) | 239 | Win | 6–3, 6–3, 6–3 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 | 140 | 2R | Sargis Sargsian | 115 | Win | 4–6, 3–6, 6–2, 6–4, 9–7 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 | 141 | 3R | David Sánchez | 89 | Win | 6–4, 6–3, 1–6, 6–3 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 | 142 | 4R | Wayne Arthurs | 59 | Win | 3–6, 6–3, 6–4, 6–2 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 28 May – 10 June 2001 | 143 | QF | Àlex Corretja (13) | 13 | Loss | 5–7, 4–6, 5–7 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 11 – 17 June 2001 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 11 – 17 June 2001 | 144 | 1R | Albert Portas | 23 | Win | 6–7$^{(4–7)}$, 6–4, 6–2 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 11 – 17 June 2001 | 145 | 2R | David Prinosil | 28 | Win | 7–6$^{(10–8)}$, 7–5 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 11 – 17 June 2001 | 146 | QF | Patrick Rafter (2) | 10 | Loss | 6–4, 6–7$^{(6–8)}$, 6–7$^{(4–7)}$ |
| Heineken Trophy 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 18 – 24 June 2001 |
| Heineken Trophy 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 18 – 24 June 2001 | 147 | 1R | Antony Dupuis | 68 | Win | 7–6$^{(7–3)}$, 6–4 |
| Heineken Trophy 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 18 – 24 June 2001 | 148 | 2R | John van Lottum (WC) | 193 | Win | 6–0, 6–1 |
| Heineken Trophy 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 18 – 24 June 2001 | 149 | QF | Raemon Sluiter | 107 | Win | 6–7$^{(4–7)}$, 6–4, 6–4 |
| Heineken Trophy 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 18 – 24 June 2001 | 150 | SF | Lleyton Hewitt (1) | 6 | Loss | 4–6, 2–6 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 | 151 | 1R | Christophe Rochus | 63 | Win | 6–2, 6–3, 6–2 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 | 152 | 2R | Xavier Malisse | 53 | Win | 6–3, 7–5, 3–6, 4–6, 6–3 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 | 153 | 3R | Jonas Björkman (33) | 41 | Win | 7–6$^{(7–4)}$, 6–3, 7–6$^{(7–2)}$ |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 | 154 | 4R | Pete Sampras (1) | 6 | Win | 7–6$^{(9–7)}$, 5–7, 6–4, 6–7$^{(2–7)}$, 7–5 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 25 June – 9 July 2001 | 155 | QF | Tim Henman (6) | 11 | Loss | 5–7, 6–7$^{(6–8)}$, 6–2, 6–7$^{(6–8)}$ |
| UBS Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 9 – 15 July 2001 |
| UBS Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 9 – 15 July 2001 | 156 | 1R | Ivan Ljubičić | 70 | Loss | 2–6, 1–6 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 27 August – 9 September 2001 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 27 August – 9 September 2001 | 157 | 1R | Lars Burgsmüller | 72 | Win | 6–4, 6–4, 6–4 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 27 August – 9 September 2001 | 158 | 2R | Robby Ginepri (WC) | 327 | Win | 6–2, 7–5, 6–1 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 27 August – 9 September 2001 | 159 | 3R | Sjeng Schalken (24) | 24 | Win | 6–4, 7–5, 7–6$^{(7–3)}$ |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 27 August – 9 September 2001 | 160 | 4R | Andre Agassi (2) | 2 | Loss | 1–6, 2–6, 4–6 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 1 – 7 October 2001 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 1 – 7 October 2001 | 161 | 1R | Nicolas Kiefer | 39 | Loss | 3–6, 6–1, 6–7$^{(4–7)}$ |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 8 – 14 October 2001 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 8 – 14 October 2001 | 162 | 1R | Nicolás Massú (LL) | 78 | Win | 4–6, 7–6$^{(10–8)}$, 6–4 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 8 – 14 October 2001 | 163 | 2R | Albert Costa | 33 | Win | 7–6$^{(7–1)}$, 6–2 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 8 – 14 October 2001 | 164 | QF | Stefan Koubek (WC) | 90 | Loss | 6–7$^{(3–7)}$, 5–7 |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 15 – 22 October 2001 |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 15 – 22 October 2001 | – | 1R | Bye | Bye | Bye | Bye |
| Stuttgart Masters Stuttgart, Germany ATP Tour Masters 1000 Hard, indoor 15 – 22 October 2001 | 165 | 2R | Wayne Ferreira | 36 | Loss | 6–7$^{(1–7)}$, 6–3, 2–6 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 | 166 | 1R | Albert Costa | 34 | Win | 6–3, 6–3 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 | 167 | 2R | Xavier Malisse | 39 | Win | 6–3, 6–4 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 | 168 | QF | Andy Roddick (6) | 16 | Win | 3–6, 6–3, 7–6$^{(7–5)}$ |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 | 169 | SF | Julien Boutter | 64 | Win | 7–6$^{(7–3)}$, 6–4 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 250 Carpet indoor 22 – 28 October 2001 | 170 | F | Tim Henman (2) | 11 | Loss (4) | 3–6, 4–6, 2–6 |
| Paris Masters Paris, France ATP Tour Masters 1000 Carpet indoor 29 October – 5 November 2001 |
| Paris Masters Paris, France ATP Tour Masters 1000 Carpet indoor 29 October – 5 November 2001 | – | 1R | Bye | Bye | Bye | Bye |
| Paris Masters Paris, France ATP Tour Masters 1000 Carpet indoor 29 October – 5 November 2001 | 171 | 2R | Jiří Novák | 40 | Loss | 4–6, 7–6$^{(7–4)}$, 6–7$^{(2–7)}$ |

#### 2002

| Tournament | Match | Round | Opponent (seed or key) | Rank | Result | Score |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 | 172 | 1R | Tommy Robredo | 34 | Win | 7–6$^{(7–5)}$, 7–6$^{(7–5)}$ |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 | 173 | 2R | Xavier Malisse | 31 | Win | 6–2, 6–4 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 | 174 | QF | Marcelo Ríos | 47 | Win | 6–7$^{(2–7)}$, 7–6$^{(7–4)}$, 6–3 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 | 175 | SF | Andy Roddick (3/WC) | 15 | Win | 7–6$^{(7–3)}$, 6–4 |
| Adidas International Sydney, Australia ATP Tour 250 Hard, outdoor 6 – 13 January 2002 | 176 | W | Juan Ignacio Chela (Q) | 67 | Win (2) | 6–3, 6–3 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 14 – 27 January 2002 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 14 – 27 January 2002 | 177 | 1R | Michael Chang | 94 | Win | 6–4, 6–4, 6–3 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 14 – 27 January 2002 | 178 | 2R | Attila Sávolt | 93 | Win | 6–2, 7–5, 6–4 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 14 – 27 January 2002 | 179 | 3R | Rainer Schüttler | 41 | Win | 7–6$^{(8–6)}$, 7–6$^{(7–5)}$, 6–4 |
| Australian Open Melbourne, Australia Grand Slam tournament Hard, outdoor 14 – 27 January 2002 | 180 | 4R | Tommy Haas (7) | 9 | Loss | 6–7$^{(3–7)}$, 6–4, 6–3, 4–6, 6–8 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 | 181 | 1R | Stefan Koubek | 50 | Win | 7–6$^{(7–2)}$, 6–3 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 | 182 | 2R | Nikolay Davydenko | 84 | Win | 6–3, 6–7$^{(4–7)}$, 7–5 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 | 183 | QF | Sargis Sargsian | 74 | Win | 4–6, 6–3, 6–3 |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 | 184 | SF | Greg Rusedski (7) | 30 | Win | 7–6$^{(9–7)}$, 7–6$^{(7–4)}$ |
| Milan Indoor Milan, Italy ATP Tour 250 Carpet, indoor 28 January – 3 February 2002 | 185 | F | Davide Sanguinetti | 87 | Loss (5) | 6–7$^{(2–7)}$, 6–4, 1–6 |
| Davis Cup, World Group Moscow, Russia Davis Cup Clay, indoor 8 – 10 February 2002 |
| Davis Cup, World Group Moscow, Russia Davis Cup Clay, indoor 8 – 10 February 2002 | 186 | 1R R1 | Marat Safin | 7 | Win | 7–5, 6–1, 6–2 |
| Davis Cup, World Group Moscow, Russia Davis Cup Clay, indoor 8 – 10 February 2002 | 187 | 1R R4 | Yevgeny Kafelnikov | 4 | Win | 7–6$^{(8–6)}$, 6–1, 6–1 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 18 – 24 February 2002 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 18 – 24 February 2002 | 188 | 1R | John van Lottum (WC) | 124 | Win | 6–3, 6–4 |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 18 – 24 February 2002 | – | 2R | Thomas Enqvist | 20 | Walkover | N/A |
| ABN AMRO World Tennis Tournament Rotterdam, Netherlands ATP Tour 500 Hard, indoor 18 – 24 February 2002 | 189 | QF | Nicolas Escudé | 22 | Loss | 6–3, 6–7$^{(8–10)}$, 5–7 |
| Dubai Tennis Championships Dubai, United Arab Emirates ATP Tour 500 Hard, outdoor 25 February – 3 March 2002 |
| Dubai Tennis Championships Dubai, United Arab Emirates ATP Tour 500 Hard, outdoor 25 February – 3 March 2002 | 190 | 1R | Adrian Voinea (Q) | 76 | Win | 6–3, 6–4 |
| Dubai Tennis Championships Dubai, United Arab Emirates ATP Tour 500 Hard, outdoor 25 February – 3 March 2002 | 191 | 2R | Rainer Schüttler | 40 | Loss | 3–6, 1–6 |
| Pacific Life Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 6 – 17 March 2002 |
| Pacific Life Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 6 – 17 March 2002 | 192 | 1R | Xavier Malisse | 32 | Win | 6–7$^{(5–7)}$, 7–6$^{(7–3)}$, 6–3 |
| Pacific Life Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 6 – 17 March 2002 | 193 | 2R | Stefan Koubek | 50 | Win | 6–4, 6–4 |
| Pacific Life Open Indian Wells, United States ATP Tour Masters 1000 Hard, outdoor 6 – 17 March 2002 | 194 | 3R | Thomas Enqvist | 22 | Loss | 4–6, 3–6 |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | – | 1R | Bye | Bye | Bye | Bye |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 195 | 2R | Jeff Morrison (Q) | 139 | Win | 6–1, 7–6$^{(8–6)}$ |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 196 | 3R | Albert Portas (23) | 25 | Win | 6–4, 6–1 |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 197 | 4R | Tim Henman (5) | 6 | Win | 6–2, retired |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 198 | QF | Andrei Pavel (26) | 28 | Win | 6–1, 6–1 |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 199 | SF | Lleyton Hewitt (1) | 1 | Win | 6–3, 6–4 |
| NASDAQ-100 Open Miami, United States ATP Tour Masters 1000 Hard, outdoor 18 – 31 March 2002 | 200 | F | Andre Agassi (9) | 10 | Loss (6) | 3–6, 3–6, 6–3, 4–6 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 15 – 21 April 2002 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 15 – 21 April 2002 | 201 | 1R | Mariano Zabaleta (Q) | 69 | Win | 7–6$^{(7–2)}$, 6–4 |
| Monte Carlo Masters Monte Carlo, Monaco ATP Tour Masters 1000 Clay, outdoor 15 – 21 April 2002 | 202 | 2R | David Nalbandian | 35 | Loss | 2–6, 1–6 |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 6 – 12 May 2002 |
| Rome Masters Rome, Italy ATP Tour Masters 1000 Clay, outdoor 6 – 12 May 2002 | 203 | 1R | Andrea Gaudenzi | 58 | Loss | 2–6, 1–6 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 204 | 1R | Nicolás Lapentti | 29 | Win | 6–1, 6–4 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 205 | 2R | Bohdan Ulihrach | 42 | Win | 6–3, 6–0 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 206 | 3R | Adrian Voinea (Q) | 67 | Win | 7–5, 6–4 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 207 | QF | Gustavo Kuerten (2) | 7 | Win | 6–0, 1–6, 6–2 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 208 | SF | Max Mirnyi | 39 | Win | 6–4, 6–4 |
| Hamburg Masters Hamburg, Germany ATP Tour Masters 1000 Clay, outdoor 13 – 19 May 2002 | 209 | W | Marat Safin (6) | 5 | Win (3) | 6–1, 6–3, 6–4 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 27 May – 9 June 2002 |
| French Open Paris, France Grand Slam tournament Clay, outdoor 27 May – 9 June 2002 | 210 | 1R | Hicham Arazi | 45 | Loss | 3–6, 2–6, 4–6 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 10 – 16 June 2002 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 10 – 16 June 2002 | 211 | 1R | Hendrik Dreekmann (WC) | – | Win | 6–7$^{(5–7)}$, 6–3, 6–4 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 10 – 16 June 2002 | 212 | 2R | David Prinosil (Q) | 206 | Win | 6–2, 6–4 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 10 – 16 June 2002 | 213 | QF | Mikhail Youzhny | 67 | Win | 6–3, 6–4 |
| Gerry Weber Open Halle, Germany ATP Tour 250 Grass, outdoor 10 – 16 June 2002 | 214 | SF | Nicolas Kiefer | 66 | Loss | 6–4, 4–6, 4–6 |
| Ordina Open 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 17 – 23 June 2002 |
| Ordina Open 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 17 – 23 June 2002 | 215 | 1R | Richard Krajicek (WC) | – | Win | 6–2, 7–5 |
| Ordina Open 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 17 – 23 June 2002 | 216 | 2R | Ivo Heuberger | 127 | Win | 6–4, retired |
| Ordina Open 's-Hertogenbosch, Netherlands ATP Tour 250 Grass, outdoor 17 – 23 June 2002 | 217 | QF | Sjeng Schalken (6) | 31 | Loss | 6–3, 5–7, 3–6 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 24 June – 7 July 2002 |
| The Championships, Wimbledon London, United Kingdom Grand Slam tournament Grass, outdoor 24 June – 7 July 2002 | 218 | 1R | Mario Ančić (Q) | 154 | Loss | 3–6, 6–7$^{(2–7)}$, 3–6 |
| Allianz Suisse Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 8 – 14 July 2002 |
| Allianz Suisse Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 8 – 14 July 2002 | 219 | 1R | Hicham Arazi | 46 | Win | 6–4, 6–3 |
| Allianz Suisse Open Gstaad, Switzerland ATP Tour 250 Clay, outdoor 8 – 14 July 2002 | 220 | 2R | Radek Štěpánek (Q) | 110 | Loss | 6–3, 3–6, 2–6 |
| Canada Masters Toronto, Canada ATP Tour Masters 1000 Hard, outdoor 29 July – 4 August 2002 |
| Canada Masters Toronto, Canada ATP Tour Masters 1000 Hard, outdoor 29 July – 4 August 2002 | 221 | 1R | Guillermo Cañas | 19 | Loss | 6–7$^{(10–12)}$, 5–7 |
| W&S Financial Group Masters Cincinnati, United States ATP Tour Masters 1000 Hard, outdoor 5 – 12 August 2002 |
| W&S Financial Group Masters Cincinnati, United States ATP Tour Masters 1000 Hard, outdoor 5 – 12 August 2002 | 222 | 1R | Ivan Ljubičić | 34 | Loss | 6–2, 4–6, 3–6 |
| TD Waterhouse Cup Long Island, United States ATP Tour 250 Hard, outdoor 19 – 25 August 2002 |
| TD Waterhouse Cup Long Island, United States ATP Tour 250 Hard, outdoor 19 – 25 August 2002 | – | 1R | Bye | Bye | Bye | Bye |
| TD Waterhouse Cup Long Island, United States ATP Tour 250 Hard, outdoor 19 – 25 August 2002 | 223 | 2R | Nicolás Massú | 65 | Loss | 7–6$^{(7–5)}$, 1–6, 3–6 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 26 August – 8 September 2002 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 26 August – 8 September 2002 | 224 | 1R | Jiří Vaněk | 157 | Win | 6–1, 6–3, 4–6, 7–5 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 26 August – 8 September 2002 | 225 | 2R | Michael Chang | 132 | Win | 6–3, 6–1, 6–3 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 26 August – 8 September 2002 | 226 | 3R | Xavier Malisse (19) | 19 | Win | 4–6, 6–3, 6–4, 6–4 |
| US Open New York City, United States Grand Slam tournament Hard, outdoor 26 August – 8 September 2002 | 227 | 4R | Max Mirnyi (32) | 34 | Loss | 3–6, 6–7$^{(5–7)}$, 4–6 |
| Davis Cup, World Group Casablanca, Morocco Davis Cup Clay, outdoor 20 – 22 September 2002 |
| Davis Cup, World Group Casablanca, Morocco Davis Cup Clay, outdoor 20 – 22 September 2002 | 228 | PO R1 | Hicham Arazi | 70 | Win | 6–3, 6–2, 6–1 |
| Davis Cup, World Group Casablanca, Morocco Davis Cup Clay, outdoor 20 – 22 September 2002 | 229 | PO R4 | Younes El Aynaoui | 19 | Win | 6–3, 6–2, 6–1 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 30 September – 6 October 2002 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 30 September – 6 October 2002 | 230 | 1R | Denis Golovanov (WC) | 167 | Win | 6–0, 6–1 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 30 September – 6 October 2002 | 231 | 2R | Jarkko Nieminen | 35 | Win | 6–1, 6–4 |
| Kremlin Cup Moscow, Russia ATP Tour 250 Carpet, indoor 30 September – 6 October 2002 | 232 | QF | Marat Safin (1) | 4 | Loss | 5–7, 4–6 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 | 233 | 1R | Željko Krajan (Q) | 115 | Win | 7–5, 6–1 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 | 234 | 2R | Tommy Robredo | 36 | Win | 6–2, 6–7$^{(5–7)}$, 6–4 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 | 235 | QF | Bohdan Ulihrach (Q) | 73 | Win | 6–3, 6–3 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 | 236 | SF | Carlos Moyá (4) | 9 | Win | 6–2, 6–3 |
| CA-TennisTrophy Vienna, Austria ATP Tour 500 Hard, indoor 7 – 13 October 2002 | 237 | W | Jiří Novák (5) | 12 | Win (4) | 6–4, 6–1, 3–6, 6–4 |
| Mutua Madrileña Masters Madrid, Spain ATP Tour Masters 1000 Hard, indoor 14 – 20 October 2002 |
| Mutua Madrileña Masters Madrid, Spain ATP Tour Masters 1000 Hard, indoor 14 – 20 October 2002 | – | 1R | Bye | Bye | Bye | Bye |
| Mutua Madrileña Masters Madrid, Spain ATP Tour Masters 1000 Hard, indoor 14 – 20 October 2002 | 238 | 2R | Marcelo Ríos | 25 | Win | 6–4, 6–2 |
| Mutua Madrileña Masters Madrid, Spain ATP Tour Masters 1000 Hard, indoor 14 – 20 October 2002 | 239 | 3R | Nicolás Lapentti | 30 | Win | 6–3, 6–4 |
| Mutua Madrileña Masters Madrid, Spain ATP Tour Masters 1000 Hard, indoor 14 – 20 October 2002 | 240 | QF | Fabrice Santoro (Q) | 50 | Loss | 5–7, 3–6 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 500 Carpet, indoor 21 – 27 October 2002 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 500 Carpet, indoor 21 – 27 October 2002 | 241 | 1R | Martin Verkerk (LL) | 92 | Win | 6–3, 6–3 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 500 Carpet, indoor 21 – 27 October 2002 | 242 | 2R | Alexander Waske (Q) | 143 | Win | 6–3, 7–6$^{(7–1)}$ |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 500 Carpet, indoor 21 – 27 October 2002 | 243 | QF | Andy Roddick (5) | 12 | Win | 7–6$^{(7–5)}$, 6–1 |
| Davidoff Swiss Indoors Basel, Switzerland ATP Tour 500 Carpet, indoor 21 – 27 October 2002 | 244 | SF | David Nalbandian (6) | 18 | Loss | 7–6$^{(7–2)}$, 5–7, 3–6 |
| BNP Paribas Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 28 October – 3 November 2002 |
| BNP Paribas Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 28 October – 3 November 2002 | – | 1R | Bye | Bye | Bye | Bye |
| BNP Paribas Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 28 October – 3 November 2002 | 245 | 2R | Xavier Malisse | 26 | Win | 6–2, 6–4 |
| BNP Paribas Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 28 October – 3 November 2002 | 246 | 3R | Tommy Haas (9) | 7 | Win | 6–2, 7–6$^{(7–2)}$ |
| BNP Paribas Masters Paris, France ATP Tour Masters 1000 Carpet, indoor 28 October – 3 November 2002 | 247 | QF | Lleyton Hewitt (1) | 1 | Loss | 4–6, 4–6 |
| Tennis Masters Cup Shanghai, China ATP Finals Hard, indoor 12 – 18 November 2002 |
| Tennis Masters Cup Shanghai, China ATP Finals Hard, indoor 12 – 18 November 2002 | 248 | RR | Juan Carlos Ferrero (4) | 4 | Win | 6–3, 6–4 |
| Tennis Masters Cup Shanghai, China ATP Finals Hard, indoor 12 – 18 November 2002 | 249 | RR | Jiří Novák (7) | 7 | Win | 6–0, 4–6, 6–2 |
| Tennis Masters Cup Shanghai, China ATP Finals Hard, indoor 12 – 18 November 2002 | 250 | RR | Thomas Johansson (9) | 14 | Win | 6–3, 7–5 |
| Tennis Masters Cup Shanghai, China ATP Finals Hard, indoor 12 – 18 November 2002 | 251 | SF | Lleyton Hewitt (1) | 1 | Loss | 5–7, 7–5, 5–7 |

## Yearly Records
### Finals
#### Singles: 10 (4–6)

* Legend
* Grand Slam (0–0)
* ATP World Tour Finals (0–0)
* ATP World Tour Masters 1000 (1–1)
* ATP World Tour 500 Series (1–1)
* ATP World Tour 250 Series (2–4)
* Titles by surface
* Hard (2–2)
* Clay (1–0)
* Grass (0–0)
* Carpet (1–4)
* Titles by surface
* Outdoors (2–1)
* Indoors (2–5)
| Outcome | No. | Date | Championship | Surface | Opponent in the final | Score in the final |
| Runner-up | 1. | February 13, 2000 | Marseille, France | Carpet (i) | Marc Rosset | 6–2, 3–6, 6–7$^{(5–7)}$ |
| Runner-up | 2. | October 29, 2000 | Basel, Switzerland | Carpet (i) | Thomas Enqvist | 2–6, 6–4, 6–7$^{(4–7)}$, 6–1, 1–6 |
| Winner | 1. | February 4, 2001 | Milan, Italy | Carpet (i) | Julien Boutter | 6–4, 6–7$^{(7–9)}$, 6–4 |
| Runner-up | 3. | February 25, 2001 | Rotterdam, Netherlands | Hard (i) | Nicolas Escudé | 5–7, 6–3, 6–7$^{(5–7)}$ |
| Runner-up | 4. | October 28, 2001 | Basel, Switzerland (2) | Carpet (i) | Tim Henman | 3–6, 4–6, 2–6 |
| Winner | 2. | January 13, 2002 | Sydney, Australia | Hard | Juan Ignacio Chela | 6–3, 6–3 |
| Runner-up | 5. | February 3, 2002 | Milan, Italy | Carpet (i) | Davide Sanguinetti | 6–7$^{(2–7)}$, 6–4, 1–6 |
| Runner-up | 6. | March 31, 2002 | Miami, United States | Hard | Andre Agassi | 3–6, 3–6, 6–3, 4–6 |
| Winner | 3. | May 19, 2002 | Hamburg, Germany | Clay | Marat Safin | 6–1, 6–3, 6–4 |
| Winner | 4. | October 13, 2002 | Vienna, Austria | Hard (i) | Jiří Novák | 6–4, 6–1, 3–6, 6–4 |