Manuel Jorquera defeated Stefano Cobolli 7-5 7-6 in the Italy 6 3 round of 32 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 3–1, but Manuel Jorquera had been the form player, winning 4 of their last 8 on clay. Manuel Jorquera narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-08-01 | Italy F24 | R32 | clay | Manuel Jorquera | 6-7(2) 6-4 6-3 |
| 2002-10-28 | Italy 8 1 | QF | hard | Stefano Cobolli | 7-5 6-3 |
| 2002-03-11 | Italy 1 2 | R32 | clay | Stefano Cobolli | 4-6 6-4 6-2 |
| 2000-06-19 | Italy 3 1 | R32 | clay | Stefano Cobolli | 6-4 6-2 |