Lisa Raymond defeated Natalia Zvereva 6-4 6-4 in the Indian Wells round of 64 on hard. The upset overturned the form book — Natalia Zvereva came in leading the head-to-head 3–1, defending last year's quarter-final. Lisa Raymond narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-19 | Eastbourne | R32 | grass | Natalia Zvereva | 7-5 6-3 |
| 2000-03-10 | Indian Wells | R64 | hard | Natalia Zvereva | 1-6 6-3 6-2 |
| 1999-02-02 | Tokyo | R16 | hard | Natalia Zvereva | 6-3 6-2 |
| 1998-08-31 | US Open | R64 | hard | Lisa Raymond | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.