Gianluca Luddi defeated Marco Monnecchi 7-6 7-6 in the Italy F12 qualifying round on clay. Gianluca Luddi extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-05 | Italy F5 | R32 | clay | Marco Monnecchi | 6-3 6-2 |
| 1997-05-31 | Italy 3 Masters 2 | R32 | clay | Gianluca Luddi | 6-2 5-7 6-0 |