Wayne Ferreira defeated Gustavo Kuerten 7-6 6-4 in the Hamburg Masters round of 16 on clay. The upset overturned the form book — Gustavo Kuerten came in leading the head-to-head 5–0, defending last year's quarter-final. Wayne Ferreira claimed a first win over Gustavo Kuerten in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-14 | Indianapolis | QF | hard | Gustavo Kuerten | 6-2 6-3 |
| 2000-05-15 | Hamburg Masters | R16 | clay | Gustavo Kuerten | 6-1 6-2 |
| 2000-03-20 | Miami Masters | QF | hard | Gustavo Kuerten | 6-3 6-1 |
| 1999-10-18 | Lyon | R16 | clay | Gustavo Kuerten | 7-6(5) 6-3 |
| 1997-03-10 | Indian Wells Masters | R32 | hard | Gustavo Kuerten | 7-6(5) 1-6 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (66 vs 115). ATP, WTA & Challenger.