Nathan Thompson defeated Leonardo Kirche 3-6 6-0 6-4 in the Brazil F16 round of 16 on clay. The upset overturned the form book — Leonardo Kirche came in leading the head-to-head 1–0. Nathan Thompson claimed a first win over Leonardo Kirche in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-09 | Brazil F14 | R16 | clay | Leonardo Kirche | 6-4 3-6 6-2 |