Anna Kournikova defeated Chanda Rubin 3-6 6-2 7-6 in the Indian Wells round of 32 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 3–1, defending last year's round of 32. Anna Kournikova extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-19 | Eastbourne | QF | grass | Chanda Rubin | 7-5 0-6 6-3 |
| 1999-06-14 | Eastbourne | R32 | grass | Anna Kournikova | 6-2 4-6 6-4 |
| 1999-02-22 | Oklahoma | QF | hard | Anna Kournikova | 7-5 0-6 6-3 |
| 1997-06-23 | Wimbledon | R128 | grass | Anna Kournikova | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.