Guillermo Duran defeated Diego Cristin 6-3 6-3 in the Argentina F16 round of 32 on clay. The upset overturned the form book — Diego Cristin came in leading the head-to-head 3–0, but Guillermo Duran had been the form player, winning 3 of their last 10 on clay. Guillermo Duran claimed a first win over Diego Cristin in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-05 | Argentina F18 FUTURES | QF | clay | Diego Cristin | 6-4 6-2 |
| 2008-05-12 | Argentina F2 | R32 | clay | Diego Cristin | 6-1 6-1 |
| 2007-05-07 | Argentina F3 | R32 | clay | Diego Cristin | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.