Martin Alund defeated Juan Pablo Amado 3-6 6-0 6-1 in the Chile F7 round of 32 on clay. The upset overturned the form book — Juan Pablo Amado came in leading the head-to-head 4–2, but Martin Alund had been the form player, winning 7 of their last 10 on clay. Martin Alund narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-14 | Paraguay F2 | SF | clay | Juan Pablo Amado | 6-4 7-6(4) |
| 2008-07-07 | Argentina F7 | QF | clay | Juan Pablo Amado | 6-4 5-7 6-2 |
| 2008-06-23 | Argentina F5 | SF | clay | Martin Alund | 6-2 6-1 |
| 2008-04-21 | Brazil F1 | R16 | clay | Juan Pablo Amado | 6-2 7-5 |
| 2006-05-15 | Argentina F7 | QF | clay | Juan Pablo Amado | 6-3 6-1 |
| 2004-09-13 | Argentina F6 | R32 | clay | Martin Alund | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.