Daniele Ceraudo defeated Alessio Di Mauro 7-6 6-2 in the Italy 2 Masters 1 round of 16 on clay. The upset overturned the form book — Alessio Di Mauro came in leading the head-to-head 1–0. Daniele Ceraudo claimed a first win over Alessio Di Mauro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 3 | R16 | clay | Alessio Di Mauro | 6-4 3-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.