Gianluca Luddi defeated Elia Grossi 6-4 7-6 in the Italy 2 3 round of 32 on clay. The upset overturned the form book — Elia Grossi came in leading the head-to-head 4–1, but Gianluca Luddi had been the form player, winning 4 of their last 6 on clay. Gianluca Luddi narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-12 | Italy F3 | R16 | clay | Elia Grossi | 6-2 7-6 |
| 1997-06-28 | Italy 4 Masters 2 | SF | clay | Elia Grossi | 6-3 7-5 |
| 1997-06-28 | Italy 4 Masters 4 | F | clay | Elia Grossi | 7-6 3-6 6-3 |
| 1997-05-31 | Italy 3 Masters 3 | R16 | clay | Elia Grossi | 6-4 6-3 |
| 1996-06-01 | Italy 2 Masters 4 | R32 | clay | Gianluca Luddi | 3-6 7-6 6-2 |