Leonardo Kirche defeated Nathan Thompson 6-4 3-6 6-2 in the Brazil F14 round of 16 on clay. The upset overturned the form book — Nathan Thompson came in leading the head-to-head 1–0. Leonardo Kirche claimed a first win over Nathan Thompson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-23 | Brazil F16 | R16 | clay | Nathan Thompson | 3-6 6-0 6-4 |