Juan Martin Aranguren defeated Cristian Villagran 2-6 6-1 6-4 in the Italy F5 round of 32 on clay. The upset overturned the form book — Cristian Villagran came in leading the head-to-head 2–1. Juan Martin Aranguren narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-11-26 | Uruguay F1 | SF | clay | Cristian Villagran | 6-7(3) 6-3 6-0 |
| 2007-04-30 | Argentina F2 | QF | clay | Juan Martin Aranguren | 6-2 6-2 |
| 2006-04-17 | Uruguay F2 | F | clay | Cristian Villagran | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.