Felipe Parada advanced when Jonathan Gonzalia retired 6-2 5-2 in the Chile F4 round of 32. Felipe Parada extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-10-29 | Chile F3 | SF | clay | Jonathan Gonzalia | 6-4 6-3 |
| 2002-09-16 | Bolivia F2 | R32 | clay | Felipe Parada | 6-1 6-4 |