Gianluca Luddi defeated Marco Monnecchi 6-2 5-7 6-0 in the Italy 3 Masters 2 round of 32 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 |
| 1999-06-14 | Italy F12 | QF | clay | Gianluca Luddi | 7-6 7-6 |