Alessio Di Mauro defeated Florian Allgauer 6-3 6-4 in the Italy 1 1 round of 16 on clay. The upset overturned the form book — Florian Allgauer came in leading the head-to-head 3–1, but Alessio Di Mauro had been the form player, winning 4 of their last 6 on clay. Alessio Di Mauro narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Italy 4 2 | QF | clay | Alessio Di Mauro | 7-5 3-0 |
| 1998-06-27 | Italy 2 Masters 2 | QF | clay | Florian Allgauer | 6-3 6-2 |
| 1998-06-27 | Italy 2 Masters 3 | QF | clay | Florian Allgauer | 6-4 6-2 |
| 1998-06-27 | Italy 2 Masters 4 | SF | clay | Florian Allgauer | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.