Anastasia Myskina defeated Angeles Montolio 6-2 4-6 6-1 in the Doha round of 32 on hard. Anastasia Myskina extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Knokke-Heist | R32 | clay | Angeles Montolio | 6-3 7-5 |
| 1999-07-12 | Palermo | F | clay | Anastasia Myskina | 3-6 7-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.