Alessio Di Mauro defeated Filippo Messori 4-6 6-4 6-4 in the Italy 5 3 final on clay. The upset overturned the form book — Filippo Messori came in leading the head-to-head 3–0, but Alessio Di Mauro had been the form player, winning 6 of their last 8 on clay. Alessio Di Mauro claimed a first win over Filippo Messori in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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 |
| 1998-04-20 | Italy F4 | R32 | clay | Filippo Messori | 6-0 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.