Andrei Medvedev defeated Yevgeny Kafelnikov 6-7 7-5 6-3 in the Stuttgart Outdoor round of 16 on clay. The upset overturned the form book — Yevgeny Kafelnikov came in leading the head-to-head 4–1. Andrei Medvedev narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-02-21 | London | R32 | carpet | Yevgeny Kafelnikov | 6-3 6-4 |
| 1999-08-30 | US Open | R16 | hard | Yevgeny Kafelnikov | 7-6(5) 6-1 6-0 |
| 1998-06-08 | Halle | R32 | grass | Yevgeny Kafelnikov | 1-6 7-5 6-1 |
| 1997-10-20 | Stuttgart Masters | R32 | carpet | Yevgeny Kafelnikov | 6-0 2-6 6-4 |
| 1997-05-05 | Hamburg Masters | SF | clay | Andrei Medvedev | 6-3 6-1 |
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 (60 vs 200). ATP, WTA & Challenger.