Jorge Aguilar defeated Diego Alvarez 6-7 6-3 6-3 in the Chile F2 semi-final on clay. The upset overturned the form book — Diego Alvarez came in leading the head-to-head 1–0, but Jorge Aguilar had been the form player, winning 7 of their last 10 on clay. Jorge Aguilar claimed a first win over Diego Alvarez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-20 | Chile F3 | SF | clay | Diego Alvarez | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.