Valentin Florez defeated Jorge Montero 6-3 7-6 in the Chile F1 round of 16 on clay. The upset overturned the form book — Jorge Montero came in leading the head-to-head 2–0, but Valentin Florez had been the form player, winning 3 of their last 5 on clay. Valentin Florez claimed a first win over Jorge Montero in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-12-02 | Chile F10 | R16 | clay | Jorge Montero | 6-2 6-0 |
| 2013-11-25 | Chile F9 | QF | clay | Jorge Montero | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.