Anna Kournikova defeated Kristina Brandi 6-3 6-1 in the Oklahoma round of 16 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 1–0. Anna Kournikova extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-18 | Key Biscayne | R64 | hard | Anna Kournikova | 6-7 6-0 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.