Courtney Nagle defeated Andrea Koch Benvenuto 7-5 6-2 in the Monterrey 10K qualifying round on hard. The upset overturned the form book — Andrea Koch Benvenuto came in leading the head-to-head 1–0. Courtney Nagle claimed a first win over Andrea Koch Benvenuto in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-05-15 | Obregon 10K | SF | hard | Andrea Koch Benvenuto | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.