Anna Kournikova defeated Amanda Coetzer 6-1 3-6 6-3 in the Key Biscayne round of 64 on hard. The upset overturned the form book — Amanda Coetzer came in leading the head-to-head 7–0, but Anna Kournikova had been the form player, winning 3 of their last 8 on hard. Anna Kournikova claimed a first win over Amanda Coetzer in eight meetings, narrowing the head-to-head to 7–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-10-15 | Zurich | R32 | hard | Amanda Coetzer | 6-0 4-6 6-3 |
| 1999-08-02 | San Diego | R16 | hard | Amanda Coetzer | 6-0 1-6 6-1 |
| 1999-02-22 | Oklahoma | SF | hard | Amanda Coetzer | 6-4 6-2 |
| 1998-08-24 | New Haven | R16 | hard | Amanda Coetzer | 1-6 6-4 7-5 |
| 1997-10-06 | Filderstadt | R16 | hard | Amanda Coetzer | 3-6 6-3 6-4 |
| 1997-05-05 | Rome | R32 | clay | Amanda Coetzer | 6-2 4-6 6-1 |
| 1997-01-13 | Australian Open | R128 | hard | Amanda Coetzer | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.