Katarina Srebotnik defeated Angeles Montolio 6-3 7-5 in the Cali 25K round of 32 on clay. The upset overturned the form book — Angeles Montolio came in leading the head-to-head 2–0. Katarina Srebotnik claimed a first win over Angeles Montolio in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-17 | Budapest | R32 | clay | Angeles Montolio | 1-6 6-2 6-4 |
| 1999-07-12 | Palermo | SF | clay | Angeles Montolio | 6-2 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.