Gianluca Luddi defeated Riccardo Capannelli 7-6 6-3 in the Italy 2 3 round of 16 on clay. The result followed the form book — Gianluca Luddi came in leading the head-to-head 1–0. Gianluca Luddi extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | R32 | clay | Gianluca Luddi | 6-4 7-6 |