Matteo Colla defeated Gianluca Luddi 6-0 7-5 in the Italy 2 3 qualifying round on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 2–1. Matteo Colla narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-31 | Italy F10 | R32 | clay | Matteo Colla | 6-4 7-5 |
| 1997-10-04 | Italy 6 Masters 1 | SF | clay | Gianluca Luddi | 6-4 1-6 6-4 |
| 1996-08-03 | Italy 4 Masters 1 | R32 | clay | Gianluca Luddi | 6-7 6-4 6-4 |