Anna Kournikova defeated Kristina Brandi 6-7 6-0 6-2 in the Key Biscayne round of 64 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 1–0, defending last year's final. Anna Kournikova extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-22 | Oklahoma | R16 | hard | Anna Kournikova | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.