| Radulescu | 1 - 0 | ||||
| 1997 | Munich | 1 | clay | W | 7-6 (7-3), 7-6 (7-5) |
| Rafter | 1 - 3 | ||||
| 2000 | Salem Open | S | hardcourt | W | 7-6 (7-2), 6-4 |
| 1998 | Canadian Open | 3 | hardcourt | L | 3-6, 3-6 |
| 1998 | US Open | F | hardcourt | L | 3-6, 6-3, 2-6, 0-6 |
| 1995 | New Haven | 1 | hardcourt | L | 4-6, 5-7 |
| Ran | 1 - 0 | ||||
| 1996 | Australian Open | 2 | hardcourt | W | 2-6, 6-4, 6-4, 6-2 |
| Raoux | 5 - 1 | ||||
| 1999 | Hopman Cup | R-R | hardcourt | W | 6-1, 6-3 |
| 1997 | Canadian Open | 2 | hardcourt | W | 7-5, 6-3 |
| 1997 | Los Angeles | Q | hardcourt | L | 6-7 (5-7), 4-6 |
| 1997 | Toulouse | 2 | hardcourt | W | 6-3, 6-7 (5-7), 6-3 |
| 1996 | Paris | 1 | carpet | W | 6-4, 6-4 |
| 1996 | Toulouse | 2 | hardcourt | W | 7-6 (7-2), 6-7 (2-7), 6-4 |
| Reid | 1 - 0 | ||||
| 2004 | Boodles & Dunthorne | RR | grass | W | 6-3, 6-3 |
| Reneberg | 3 - 0 | ||||
| 1999 | World Team Championships | RR | hardcourt | W | 6-4, 6-7 (3-7), 7-5 |
| 1997 | Scottsdale | F | hardcourt | W | 6-4, 7-6 (7-4) |
| 1997 | Lyon | 2 | carpet | W | 4-6, 7-6 (8-6), 6-4 |
| Rikl | 1 - 0 | ||||
| 1997 | Davis Cup | 1 | grass | W | 6-1, 6-4, 2-6, 6-4 |
| Rios | 2 - 4 | ||||
| 2000 | Cincinnati | 2 | hardcourt | W | 6-7 (3-7), 6-4, 7-6 (7-4) |
| 1999 | Monte Carlo | Q | clay | L | 2-6, 7-6 (7-2), 4-6 |
| 1998 | Grand Slam Cup | S | hardcourt | L | 6-7 (4-7), 3-6, 4-6 |
| 1998 | Kroger St Jude | S | hardcourt | W | 6-4, 7-6 (7-5) |
| 1995 | Malaysia | F | hardcourt | L | 6-7 (6-8), 2-6 |
| 1995 | Bologna | S | clay | L | 4-6, 6-7 (6-8) |
| Robredo | 1 - 1 | ||||
| 2006 | SAP Open | 1 | hardcourt | W | 3-6, 7-5, 7-5 |
| 2004 | Rome Masters | 1 | clay | L | 2-6, 6-4, 4-6 |
| C. Rochus | 2 - 1 | ||||
| 2005 | Ordina Open | 1 | grass | W | 6-3, 7-6 (10-8) |
| 2005 | Nasdaq 100 | 1 | hardcourt | W | 6-4, 6-2 |
| 2005 | Pro Tennis World Open (Challenger) | 2 | hardcourt | L | 7-6 (7-5), 3-6, 2-6 |
| O. Rochus | 1 - 1 | ||||
| 2004 | Wimbledon | 1 | grass | W | 6-3, 6-4, 6-2 |
| 2004 | Dubai | 1 | hardcourt | L | 2-6, 6-7 (8-10) |
| Roddick | 0 - 1 | ||||
| 2005 | Stella Artois | 2 | grass | L | 2-6, 4-6 |
| Rosset | 3 - 0 | ||||
| 2000 | Rome | 1 | clay | W | 6-3, 1-6, 7-6 (7-2) |
| 1996 | New Haven | Q | hardcourt | W | 6-2, 6-3 |
| 1996 | Toronto | 2 | hardcourt | W | 6-3, 3-6, 7-6 (8-6) |
| Rusedski | 3 - 3 | ||||
| 2004 | Adidas International | 2 | hardcourt | W | 6-3, 1-6, 6-4 |
| 2002 | Stella Artois | 2 | grass | W | 6-7 (1-7), 7-6 (7-3), 7-6 (7-5) |
| 2002 | Australian Open | 2 | hardcourt | L | 6-7 (7-9), 3-6, 4-6 |
| 1999 | Wimbledon | 4 | grass | W | 2-6, 7-6 (7-4), 6-3, 6-1 |
| 1997 | Wimbledon | 1 | grass | L | 6-7 (6-8), 6-7 (6-8), 3-6 |
| 1997 | Swiss Indoors | F | carpet | L | 3-6, 6-7 (6-8), 6-7 (3-7) |
| Ruud | 1 - 0 | ||||
| 1998 | US Open | 1 | hardcourt | W | 7-5, 6-4, 6-3 |