Anna Kournikova defeated Barbara Schett 6-3 7-6 in the Filderstadt round of 32 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 4–1. Anna Kournikova extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-01-15 | Australian Open | R32 | hard | Anna Kournikova | 2-6 6-4 6-3 |
| 1999-03-29 | Hilton Head | R16 | clay | Anna Kournikova | 7-6 6-4 |
| 1999-03-18 | Key Biscayne | R16 | hard | Barbara Schett | 6-1 1-6 6-1 |
| 1998-10-05 | Filderstadt | R32 | hard | Anna Kournikova | 1-6 6-4 7-6 |
| 1998-08-24 | New Haven | R32 | hard | Anna Kournikova | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.