Leonardo Kirche defeated Juan Martin Aranguren 6-4 0-6 7-6 in the Argentina F8 qualifying round on clay. The upset overturned the form book — Juan Martin Aranguren came in leading the head-to-head 2–1. Leonardo Kirche narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-03-27 | Argentina F3 | R32 | clay | Juan Martin Aranguren | 6-2 6-4 |
| 2006-01-23 | Colombia F1 | R16 | clay | Leonardo Kirche | 4-6 6-4 6-1 |
| 2002-08-26 | Brazil F3 | R32 | hard | Juan Martin Aranguren | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.