Andrei Medvedev defeated Richard Krajicek 6-4 3-6 6-1 7-6 in the US Open round of 16 on hard. The upset overturned the form book — Richard Krajicek came in defending last year's round of 16. Andrei Medvedev extended 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 |
| 1998-08-10 | Cincinnati Masters | R32 | hard | Richard Krajicek | 6-3 6-7 6-3 |
| 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 |
Averages over each player's completed matches in the selected window (198 vs 200). 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