Diego Cristin defeated Damian Guichonet 6-3 6-1 in the Uruguay F3 round of 16 on clay. The upset overturned the form book — Damian Guichonet came in leading the head-to-head 2–0. Diego Cristin claimed a first win over Damian Guichonet in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-11 | Argentina F5 | R32 | clay | Damian Guichonet | 1-6 7-6(5) 6-1 |
| 2008-11-24 | Uruguay F1 | R16 | clay | Damian Guichonet | 6-3 6-1 |