Damian Guichonet defeated Diego Cristin 6-3 6-1 in the Uruguay F1 round of 16 on clay. Damian Guichonet extended 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 |
| 2006-11-20 | Uruguay F3 | R16 | clay | Diego Cristin | 6-3 6-1 |