Caio Burjaili defeated Leonardo Kirche 7-6 4-6 6-3 in the Brazil F4 round of 32 on hard. The upset overturned the form book — Leonardo Kirche came in leading the head-to-head 1–0. Caio Burjaili claimed a first win over Leonardo Kirche in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-09 | Brazil F8 | R32 | clay | Leonardo Kirche | 6-3 6-3 |