Karen Castiblanco defeated Andrea Koch Benvenuto 6-4 6-4 in the Florianopolis 10K round of 32 on clay. The upset overturned the form book — Andrea Koch Benvenuto came in leading the head-to-head 6–0. Karen Castiblanco claimed a first win over Andrea Koch Benvenuto in seven meetings, narrowing the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-07-25 | Campos Do Jordao 25K | R16 | hard | Andrea Koch Benvenuto | 6-1 6-2 |
| 2009-11-02 | Bogota 10K | SF | clay | Andrea Koch Benvenuto | 6-3 6-1 |
| 2009-03-23 | Lima 10K | R32 | clay | Andrea Koch Benvenuto | 7-6(2) 7-6(2) |
| 2008-10-27 | Lima 10K | R32 | clay | Andrea Koch Benvenuto | 6-3 7-6(4) |
| 2007-08-27 | Santa Cruz 10K | R16 | clay | Andrea Koch Benvenuto | 6-4 6-3 |
| 2006-05-01 | Mazatlan 10K | R16 | hard | Andrea Koch Benvenuto | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.