Anne Kremer defeated Anna Kournikova 4-6 6-2 7-5 in the Filderstadt round of 32 on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 4–0, defending last year's round of 32. Anne Kremer claimed a first win over Anna Kournikova in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-01-29 | Tokyo | QF | hard | Anna Kournikova | 6-4 6-2 |
| 2000-04-10 | Amelia Island | R32 | clay | Anna Kournikova | 7-5 7-6(4) |
| 2000-02-07 | Paris | R16 | carpet | Anna Kournikova | 7-6(2) 6-2 |
| 1999-11-01 | Leipzig | R32 | carpet | Anna Kournikova | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.