Florian Allgauer defeated Gianluca Luddi 3-6 6-0 7-6 in the Italy 4 1 qualifying round on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 3–0. Florian Allgauer claimed a first win over Gianluca Luddi in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-07-27 | Italy F11 | SF | clay | Gianluca Luddi | 4-6 6-3 6-0 |
| 1998-06-27 | Italy 2 Masters 4 | F | clay | Gianluca Luddi | 6-3 6-4 |
| 1996-09-28 | Italy 5 Masters 3 | R32 | clay | Gianluca Luddi | 6-2 6-4 |