Bruno Tiberti defeated Gonzalo Tur 7-5 6-7 6-3 in the Chile F5 semi-final on clay. The upset overturned the form book — Gonzalo Tur came in leading the head-to-head 2–1, but Bruno Tiberti had been the form player, winning 4 of their last 8 on clay. Bruno Tiberti narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Argentina F9 | R32 | clay | Gonzalo Tur | 6-2 7-5 |
| 2008-12-08 | Argentina F18 | R32 | clay | Bruno Tiberti | 3-6 7-5 6-3 |
| 2008-11-10 | Argentina F16 | QF | clay | Gonzalo Tur | 6-3 6-4 |