Jimy Szymanski defeated Toshihide Matsui 6-4 6-1 in the Venezuela 1 Satellite 3 round of 32 on hard. Jimy Szymanski extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-02 | Venezuela 1 Satellite 4 | QF | hard | Toshihide Matsui | 6-4 6-4 |
| 2003-08-11 | USA F24 | QF | hard | Jimy Szymanski | 7-6(5) 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.