Giacomo Oradini defeated Davide Della Tommasina 7-6 4-6 6-3 in the Italy F2 round of 16 on hard. The upset overturned the form book — Davide Della Tommasina came in leading the head-to-head 1–0. Giacomo Oradini claimed a first win over Davide Della Tommasina in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-30 | Italy F20 | R32 | clay | Davide Della Tommasina | 6-2 6-2 |