| 2000-12-08 | Davis Cup WG F: ESP vs AUS | Clay | RR | 7 |  Lleyton Hewitt | 26 |  Albert Costa | 3-6 6-1 2-6 6-4 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 2000-12-08 | Davis Cup WG F: ESP vs AUS | Clay | RR | 12 | Juan Carlos Ferrero | 7 | Lleyton Hewitt | 6-2 7-6(5) 4-6 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 2000-11-27 | Tennis Masters Cup | Hard | RR | 7 | Alex Corretja (7) | 6 | Lleyton Hewitt (6) | 3-6 7-6(3) 6-3 | H2H | 3 | - | - | - | - | - | - | - |
| 2000-11-27 | Tennis Masters Cup | Hard | RR | 6 | Lleyton Hewitt (6) | 3 |  Pete Sampras (3) | 7-5 6-0 | H2H | 3 | - | - | - | - | - | - | - |
| 2000-11-27 | Tennis Masters Cup | Hard | RR | 1 |  Marat Safin (1) | 6 | Lleyton Hewitt (6) | 6-4 6-4 | H2H | 3 | - | - | - | - | - | - | - |
| 2000-10-30 | Stuttgart Masters | Hard | F | 19 |  Wayne Ferreira | 8 | Lleyton Hewitt (8) | 7-6(6) 3-6 6-7(5) 7-6(2) 6-2 | H2H | 5 | 251 | 18 | 5 | 51.5% | 69.0% | 55.3% | 14/20 |
| 2000-10-30 | Stuttgart Masters | Hard | SF | 8 | Lleyton Hewitt (8) | 5 | Yevgeny Kafelnikov (6) | 6-4 6-7(5) 6-3 | H2H | 3 | 124 | 7 | 4 | 45.7% | 83.7% | 60.8% | 3/4 |
| 2000-10-30 | Stuttgart Masters | Hard | QF | 8 | Lleyton Hewitt (8) | 89 |  Greg Rusedski | 6-4 6-4 | H2H | 3 | 71 | 5 | 3 | 60.7% | 88.2% | 59.1% | 0/0 |
| 2000-10-30 | Stuttgart Masters | Hard | R16 | 8 | Lleyton Hewitt (8) | 10 | Tim Henman (9) | 3-6 6-3 6-4 | H2H | 3 | 131 | 4 | 3 | 60.2% | 72.0% | 54.5% | 4/7 |
| 2000-10-30 | Stuttgart Masters | Hard | R32 | 8 | Lleyton Hewitt (8) | 37 |  Richard Krajicek | 6-4 7-5 | H2H | 3 | 83 | 9 | 3 | 50.8% | 87.5% | 64.5% | 3/3 |
