Angeles Montolio defeated Anastasia Myskina 6-3 7-5 in the Knokke-Heist round of 32 on clay. The upset overturned the form book — Anastasia Myskina came in leading the head-to-head 2–0. Angeles Montolio claimed a first win over Anastasia Myskina in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-02-11 | Doha | R32 | hard | Anastasia Myskina | 6-2 4-6 6-1 |
| 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.