Alejandro Fabbri defeated Jorge Aguilar 4-6 6-2 7-5 in the Chile F3 round of 32 on clay. The upset overturned the form book — Jorge Aguilar came in leading the head-to-head 3–0. Alejandro Fabbri claimed a first win over Jorge Aguilar in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-02-09 | Colombia F2 | R32 | hard | Jorge Aguilar | 6-4 7-5 |
| 2005-08-22 | Argentina F8 | R32 | clay | Jorge Aguilar | 5-7 6-2 7-5 |
| 2004-04-26 | Argentina F1 | R32 | clay | Jorge Aguilar | 6-1 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.