Gianluca Luddi defeated Bastian Gronefeld 6-3 7-6 in the Italy 4 2 qualifying round on clay. The upset overturned the form book — Bastian Gronefeld came in leading the head-to-head 1–0, but Gianluca Luddi had been the form player, winning 5 of their last 7 on clay. Gianluca Luddi claimed a first win over Bastian Gronefeld in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Italy 3 4 | QF | clay | Bastian Gronefeld | 7-5 7-5 |