Gianluca Luddi defeated Miguel Pastura 6-3 6-3 in the Italy 2 Masters 4 qualifying round 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 |
|---|---|---|---|---|---|
| 1999-06-07 | Italy F11 | R16 | clay | Gianluca Luddi | 6-2 3-6 6-3 |