Bastian Gronefeld defeated Stefano Cobolli 6-1 3-6 6-1 in the Italy 4 3 round of 32 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Bastian Gronefeld had been the form player, winning 3 of their last 7 on clay. Bastian Gronefeld claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Italy 3 1 | SF | clay | Stefano Cobolli | 6-2 7-5 |