Ivan Endara defeated Benjamin Dracos 6-1 6-3 in the Venezuela F9 round of 16 on clay. The upset overturned the form book — Benjamin Dracos came in leading the head-to-head 2–0. Ivan Endara claimed a first win over Benjamin Dracos in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-07 | Peru F2 | SF | clay | Benjamin Dracos | 2-6 7-6(4) 6-0 |
| 2007-11-19 | Venezuela F10 | R32 | clay | Benjamin Dracos | 6-4 4-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.