Karol Kucera defeated Gustavo Kuerten 6-4 0-6 6-2 in the Monte Carlo Masters round of 64 on clay. The upset overturned the form book — Gustavo Kuerten came in leading the head-to-head 3–1, defending the title. Karol Kucera narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-07 | Davis Cup WG QF: BRA vs SVK | RR | clay | Gustavo Kuerten | 2-6 6-3 4-6 7-5 6-1 |
| 1999-05-10 | Rome Masters | QF | clay | Gustavo Kuerten | 3-6 6-4 7-5 |
| 1999-01-11 | Sydney | QF | hard | Karol Kucera | 3-6 6-4 6-1 |
| 1998-07-20 | Stuttgart Outdoor | F | clay | Gustavo Kuerten | 4-6 6-2 6-4 |
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 (173 vs 200). ATP, WTA & Challenger.