Olga Vymetalkova defeated Mara Santangelo 1-6 6-1 6-1 in the Valladolid 25K round of 16 on hard. The upset overturned the form book — Mara Santangelo came in leading the head-to-head 2–0, but Olga Vymetalkova had been the form player, winning 2 of their last 4 on hard. Olga Vymetalkova claimed a first win over Mara Santangelo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-03-28 | Poza Rica 25K | R16 | hard | Mara Santangelo | 6-1 6-4 |
| 1999-07-19 | Brussels 10K | R16 | clay | Mara Santangelo | 7-5 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.