Filippo Messori defeated Leonardo Azzaro 6-2 7-5 in the Italy F1 round of 32 on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 2–0. Filippo Messori extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Italy F1 | R32 | clay | Filippo Messori | 7-5 6-7 6-0 |
| 1998-11-07 | Egypt 2 Masters 4 | QF | hard | Filippo Messori | 3-6 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.