Gianluca Luddi defeated Paul Hartveg 6-4 6-2 in the Italy 5 Masters 2 round of 32 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 |
|---|---|---|---|---|---|
| 1999-06-14 | Italy F12 | R32 | clay | Gianluca Luddi | 6-3 6-1 |