Filippo Messori defeated Alessio Di Mauro 6-0 6-2 in the Italy F4 round of 32 on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 2–1. Filippo Messori extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Italy 5 3 | F | clay | Alessio Di Mauro | 4-6 6-4 6-4 |
| 2000-08-21 | Italy 4 4 | F | clay | Filippo Messori | 6-4 6-1 |
| 1998-11-07 | Egypt 2 Masters 2 | QF | hard | Filippo Messori | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.