Leonardo Kirche defeated Emiliano Massa 2-6 6-3 6-4 in the Argentina F11 round of 16 on clay. The upset overturned the form book — Emiliano Massa came in leading the head-to-head 1–0, but Leonardo Kirche had been the form player, winning 3 of their last 7 on clay. Leonardo Kirche claimed a first win over Emiliano Massa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-31 | Argentina F10 | R32 | clay | Emiliano Massa | 3-6 6-4 7-5 |