Jorge Aguilar defeated Federico Cavallero 2-6 7-5 6-3 in the Chile F5 qualifying round on clay. The result followed the form book — Jorge Aguilar came in leading the head-to-head 3–0. Jorge Aguilar extended the head-to-head to 4–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-08 | Argentina F8 | R16 | clay | Jorge Aguilar | 4-6 6-3 6-2 |
| 2007-11-19 | Chile F6 | QF | clay | Jorge Aguilar | 6-4 6-3 |
| 2006-05-22 | Argentina F8 | R16 | clay | Jorge Aguilar | 4-6 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.