Aleksandrina Naydenova defeated Andrea Benitez 3-6 6-1 6-2 in the Padova 25K round of 16 on clay. The upset overturned the form book — Andrea Benitez came in leading the head-to-head 2–1. Aleksandrina Naydenova narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-03-07 | Concepcion 10K | F | clay | Aleksandrina Naydenova | 1-6 6-4 6-4 |
| 2010-09-20 | Mazatlan 10K | R16 | hard | Andrea Benitez | 6-2 6-4 |
| 2008-05-05 | Buenos Aires 10K | R32 | clay | Andrea Benitez | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.