Diego Alvarez defeated Gianluca Luddi 6-2 7-6 in the Italy 5 4 qualifying round on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 2–0. Diego Alvarez claimed a first win over Gianluca Luddi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Italy 3 1 | QF | clay | Gianluca Luddi | 6-2 3-6 6-1 |
| 2001-04-02 | Italy 2 4 | R32 | clay | Gianluca Luddi | 6-3 6-0 |