Diego Alvarez defeated Jorge Aguilar 6-3 6-3 in the Chile F3 semi-final on clay. The upset overturned the form book — Jorge Aguilar came in leading the head-to-head 1–0. Diego Alvarez claimed a first win over Jorge Aguilar in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-13 | Chile F2 | SF | clay | Jorge Aguilar | 6-7(7) 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.