Barbara Schett defeated Anna Kournikova 6-1 1-6 6-1 in the Key Biscayne round of 16 on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 5–0, defending last year's final. Barbara Schett claimed a first win over Anna Kournikova in six meetings, narrowing 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 |
| 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 |
| 1997-10-06 | Filderstadt | R32 | hard | Anna Kournikova | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.