Nicolas Kiefer defeated Karol Kucera 2-6 6-3 6-4 in the Milan quarter-final on carpet. The upset overturned the form book — Karol Kucera came in leading the head-to-head 6–1. Nicolas Kiefer narrowed the head-to-head to 6–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-04-30 | Mallorca | R32 | grass | Nicolas Kiefer | 6-4 6-2 |
| 2001-04-23 | Barcelona | R64 | clay | Karol Kucera | 6-2 6-4 |
| 1999-10-04 | Basel | SF | hard | Karol Kucera | 6-4 6-3 |
| 1999-03-08 | Indian Wells Masters | R16 | hard | Karol Kucera | 6-4 3-6 6-4 |
| 1998-05-18 | Dusseldorf | RR | clay | Karol Kucera | 6-4 6-2 |
| 1998-01-12 | Sydney Outdoor | R16 | hard | Karol Kucera | 5-0 RET |
| 1997-07-14 | Stuttgart Outdoor | R64 | clay | Karol Kucera | 1-2 RET |
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 (200 vs 200). ATP, WTA & Challenger.