Gianluca Luddi defeated Alessio Di Mauro 4-6 7-5 7-5 in the Portugal F2 round of 16 on clay. The result followed the form book — Gianluca Luddi came in leading the head-to-head 2–0. Gianluca Luddi extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | SF | clay | Gianluca Luddi | 6-3 6-2 |
| 1997-10-04 | Italy 6 Masters 1 | R16 | clay | Gianluca Luddi | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.