Rodrigo Antonio Grilli defeated Leonardo Kirche 6-4 6-0 in the Mexico F8 qualifying round on hard. The upset overturned the form book — Leonardo Kirche came in leading the head-to-head 1–0. Rodrigo Antonio Grilli claimed a first win over Leonardo Kirche in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-30 | Brazil F11Ribeirao PretoSP | SF | clay | Leonardo Kirche | 6-1 6-4 |