| Sa | 1 - 0 | ||||
| 2000 | Legg Mason Tennis Classic | 2 | hard | L | 1-6, 6-7 (10-12) |
| Safin | 1 - 5 | ||||
| 2005 | Wimbledon | 2 | grass | L | 6-7 (4-7), 6-7 (4-7), 4-6 |
| 2003 | Indian Wells | 2 | hard | L | 4-6, 3-6 |
| 2002 | Nasdaq 100 | 2 | hard | L | 6-7 (4-7), 1-6 |
| 2000 | Paris Indoors | F | carpet | L | 6-3, 6-7 (7-9), 4-6, 6-3, 6-7 (8-10 |
| 1999 | Lipton | 3 | hardcourt | L | 6-7 (4-7), 6-7 (3-7) |
| 1999 | Indian Wells | 3 | hardcourt | W | 6-4, 6-3 |
| Sampras | 5 - 7 | ||||
| 2000 | Kooyong Colonial Classic | S | hardcourt | W | 7-6 (7-4), 7-6 (7-5) |
| 2000 | French Open | 1 | clay | W | 4-6, 7-5, 7-6 (7-4), 6-4, 8-6 |
| 1999 | SyBase Open | S | hardcourt | W | (Walkover) |
| 1999 | Wimbledon | Q | grass | L | 6-3, 1-2 (retired) |
| 1998 | Wimbledon | Q | grass | L | 6-7 (7-5), 4-6, 4-6 |
| 1998 | Paris Open | Q | carpet | L | 3-6, 3-6 |
| 1997 | ATP Championship | R-R | hardcourt | W | 4-6, 6-4, 0-1 (retired) |
| 1997 | Davis Cup - Semis | RR | hardcourt | L | 1-6, 2-6, 6-7 |
| 1996 | US Open | 4 | hardcourt | L | 3-6, 3-6, 4-6 |
| 1996 | Wimbledon | 2 | grass | L | 6-7 (4-7), 4-6, 4-6 |
| 1996 | Australian Open | 3 | hardcourt | W | 4-6, 6-7 (9-11), 6-7 (3-7) |
| 1995 | US Open | 3 | hardcourt | L | 7-6 (7-5), 5-7, 5-7, 3-6 |
| Salzenstein | 1 - 0 | ||||
| 2003 | Heineken Open | 2 | hardcourt | W | 6-2, 7-5 |
| Sanguinetti | 3 - 0 | ||||
| 2006 | Nasdaq 100 - Miami | 1 | hard | W | 6-4, 4-6, 6-3 |
| 2005 | Ordina Open | Q | grass | W | 7-6 (7-0), 7-6 (7-2) |
| 2001 | Kroger St Jude | F | hardcourt | W | 6-3, 6-7 (4-7), 6-3 |
| Santoro | 5 - 2 | ||||
| 2004 | Australian Open | 2 | hardcourt | W | 4-6, 6-3, 6-4, 6-2 |
| 2002 | Masters Series - Cincinnati | 1 | hardcourt | W | 4-6, 7-6 (7-2), 6-3 |
| 1998 | Eurocard Open | 1 | hardcourt | W | 6-1, 5-7, 6-2 |
| 1997 | Stuttgard | 1 | carpet | L | 6-7 (6-8), 1-6 |
| 1997 | Lyon | S | carpet | L | 4-6, 2-6 |
| 1997 | Swiss Indoors | 2 | carpet | W | 6-3, 6-3 |
| 1996 | Toulouse | 1 | hardcourt | W | 6-3, 3-6, 7-6 (7-1) |
| Sargsian | 1 - 2 | ||||
| 2003 | Australian Open | 3 | hardcourt | L | 7-5, 5-7, 0-6, 4-6 |
| 2000 | Toronto | 1 | hardcourt | L | 4-6, 6-7 (6-8) |
| 1999 | SyBase Open | 1 | hardcourt | W | 6-7 (2-7), 7-5), 6-3 |
| 1996 | Stuttgart | 1 | hardcourt | L | 5-7, 3-6 |
| Saulnier | 2 - 1 | ||||
| 2003 | Japan Open | Q | hardcourt | L | 2-5 (retired) |
| 2003 | Wimbledon | 2 | grass | W | 6-3, 6-2, 7-6 (7-2) |
| 2000 | Ericsson Open | 2 | hardcourt | W | 4-6, 6-3, 6-4 |
| Schalen | 1 - 0 | 1998 | Kroger St Jude | 3 | hardcourt | W | 6-4, 6-4 |
| Schalken | 5 - 3 | ||||
| 2002 | US Open | 1 | hardcourt | L | 7-6 (7-1), 6-4, 3-6, 3-5 (retired) |
| 2004 | ATP World Team Cup | RR-2 | Clay | W | 4-6, 7-6 (7-4), 7-5 |
| 2002 | Australian Mens Hardcourt | 2 | hardcourt | W | 6-0, 6-3 |
| 2000 | Japan Open | Q | hardcourt | L | 3-6, 2-6 |
| 2000 | Wimbledon | 3 | grass | W | 4-6, 6-3, 6-7 (7-9), 7-6 (7-4), 20-18 |
| 2000 | Indian Wells | Q | hardcourt | W | 7-6 (9-7), 6-4 |
| 1997 | Cincinnati | 1 | hardcourt | L | 6-7 (5-7), 3-6 |
| 1996 | Toronto | 1 | hardcourt | W | 6-3, 6-4 |
| Schaller | 1 - 0 | ||||
| 1996 | Monte Carlo | 1 | clay | W | 2-6, 7-6 (7-3), 7-6 (7-4) |
| Schuettler | 0 - 3 | ||||
| 2003 | Tata Open | 3 | hardcourt | L | 2-6, 1-6 |
| 2002 | RCA Championships | 1 | hardcourt | L | 6-7 (2-7), 6-7 (4-7) |
| 2001 | Salem Open | 2 | hardcourt | L | 6-7 (5-7), 6-4, 3-6 |
| Shelton | 1 - 0 | ||||
| 1997 | Scottsdale | 2 | hardcourt | W | 6-4, 6-1 |
| Simerink | 1 - 0 | ||||
| 1997 | French Open | 3 | clay | W | 6-4, 6-4, 6-2 |
| Sinner | 0 - 1 | ||||
| 1995 | Essen | 1 | carpet | L | 6-3, 3-6, 4-6 |
| Sluiter | 3 - 0 | ||||
| 2005 | Stella Artois | 1 | grass | W | 6-4, 6-0 |
| 2003 | Tennis Masters - Hamburg | 1 | clay | W | 6-4, 7-5 |
| 2000 | Australian Open | 2 | hardcourt | W | 6-1, 2-6, 7-6 (7-4), 6-1 |
| Soderling | 1 - 1 | ||||
| 2003 | SAP Open | 2 | hardcourt | L | 2-6, 3-6 |
| 2003 | Heineken Open | S | hardcourt | W | 6-4, 6-4 |
| Spadea | 5 - 2 | ||||
| 2006 | Adeliade International | 1 | hard | W | 6-3. 4-6, 6-3 |
| 2004 | World Team Cup | RR-1 | clay | W | 6-7 (1-7), 6-3, 7-6 (7-4) |
| 2002 | Rome | 1 | clay | W | 6-2, 6-2 |
| 1999 | Rome | 1 | clay | L | 6-7 (2-7), 6-4, 1-6 |
| 1998 | SyBase Open | 1 | hardcourt | L | 4-6, 3-6 |
| 1997 | Toulouse | S | hardcourt | W | 7-5, 6-4 |
| 1995 | Scottsdale | 1 | hardcourt | W | 6-2, 6-1 |
| Squillari | 1 - 0 | ||||
| 1998 | Scottsdale | 1 | hardcourt | W | 6-2, 7-5 |
| Srichaphan | 2 - 0 | ||||
| 2002 | Australian Open | 2 | hardcourt | W | 3-6, 6-1, 1-6, 7-5, 6-3 |
| 2000 | Hopman Cup | R-R | hardcourt | W | 6-1, 6-4 |
| Stafford | 1 - 1 | ||||
| 1998 | Indianapolis | 1 | hardcourt | W | 6-3, 6-2 |
| 1994 | Australian Open | 1 | hardcourt | L | 2-6, 2-6, 0-6 |
| Stark | 1 - 0 | ||||
| 1997 | Stella Artois | 2 | grass | W | 7-6 (12-10), 3-6, 6-3 |
| Stephanik | 1 - 0 | ||||
| 2003 | Wimbledon | 3 | grass | W | 4-6, 7-6 (9-7), 6-4, 7-6 (8-6) |
| Steven | 1 - 0 | ||||
| 1995 | Tokyo | 3 | carpet | W | 7-6 (7-4), 6-3 |
| Stolle | 1 - 0 | ||||
| 1997 | Los Angeles | 2 | hardcourt | W | 4-6, 6-4, 6-3 |
| Stoltenberg | 1 - 2 | ||||
| 1999 | French Open | 1 | clay | L | 6-7 (4-7), 4-6, 1-6 |
| 1998 | Wimbledon | 4 | grass | W | 5-7, 6-1, 6-3, 6-3 |
| 1996 | Vienna | 1 | carpet | L | 4-6, 6-7 (7-9) |