Leonardo Olguin advanced when Patricio Rudi retired 6-1 3-2 in the Paraguay F1 qualifying round. Leonardo Olguin narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-11-18 | Uruguay F2 | SF | clay | Patricio Rudi | 6-3 6-1 |
| 2000-05-22 | Argentina F6 | QF | clay | Patricio Rudi | 6-2 6-1 |
| 1999-10-18 | Paraguay F2 | R16 | clay | Leonardo Olguin | 7-6 5-7 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.