Marco Monnecchi defeated Gianluca Luddi 6-3 6-2 in the Italy F5 round of 32 on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 2–0. Marco Monnecchi claimed a first win over Gianluca Luddi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Italy F12 | QF | clay | Gianluca Luddi | 7-6 7-6 |
| 1997-05-31 | Italy 3 Masters 2 | R32 | clay | Gianluca Luddi | 6-2 5-7 6-0 |