Guillermo Duran advanced past Cristhian Ignacio Benedetti via walkover in the Argentina F15 qualifying round. Guillermo Duran extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-06-13 | Argentina F7 | R16 | clay | Guillermo Duran | 6-2 6-1 |
| 2009-09-21 | Argentina F16 | R16 | clay | Guillermo Duran | 6-4 6-2 |
| 2008-06-30 | Peru F1 | R16 | clay | Cristhian Ignacio Benedetti | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.