Richard Krajicek defeated Andrei Medvedev 6-3 6-7 6-3 in the Cincinnati Masters round of 32 on hard. The upset overturned the form book — Andrei Medvedev came in leading the head-to-head 3–1, defending last year's round of 16. Richard Krajicek narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Grand Slam Cup | QF | carpet | Andrei Medvedev | 7-6 6-4 |
| 1997-05-05 | Hamburg Masters | R32 | clay | Andrei Medvedev | 6-1 6-1 |
| 1995-02-27 | Rotterdam | QF | hard | Richard Krajicek | 7-6(5) 6-4 |
| 1993-08-30 | US Open | R16 | hard | Andrei Medvedev | 6-4 3-6 6-1 7-6(4) |
Averages over each player's completed matches in the selected window (191 vs 145). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About