Chanda Rubin defeated Anna Kournikova 7-5 0-6 6-3 in the Eastbourne quarter-final on grass. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 4–0, defending last year's semi-final. Chanda Rubin claimed a first win over Anna Kournikova in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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 |
| 1998-03-05 | Indian Wells | R32 | hard | Anna Kournikova | 3-6 6-2 7-6 |
| 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.