Diego Cristin defeated Jorge Aguilar 7-5 6-4 in the Chile F4 semi-final on clay. The upset overturned the form book — Jorge Aguilar came in leading the head-to-head 1–0. Diego Cristin claimed a first win over Jorge Aguilar in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-26 | Chile F4 | R16 | clay | Jorge Aguilar | 7-5 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.