Toshihide Matsui defeated Jimy Szymanski 6-4 6-4 in the Venezuela 1 Satellite 4 qualifying round on hard. The upset overturned the form book — Jimy Szymanski came in leading the head-to-head 2–0. Toshihide Matsui claimed a first win over Jimy Szymanski in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-02 | Venezuela 1 Satellite 3 | R32 | hard | Jimy Szymanski | 6-4 6-1 |
| 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.