Jimy Szymanski defeated Bertrand Madsen 6-4 6-4 6-1 in the HAI vs VEN round robin on clay. The result followed the form book — Jimy Szymanski came in leading the head-to-head 1–0. Jimy Szymanski extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-12 | Germany F2 | R32 | clay | Jimy Szymanski | 6-7 7-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.