Filippo Messori defeated Martin Vassallo Arguello 1-6 6-2 6-3 in the Chile F6 qualifying round on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 1–0. Filippo Messori extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Argentina F4 | R32 | clay | Filippo Messori | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.