Paolo Lorenzi defeated Stefano Cobolli 3-6 7-6 6-0 in the Milan q32 on carpet. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 3–1. Paolo Lorenzi narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-09-22 | Palermo | Q16 | clay | Paolo Lorenzi | 7-6(5) 7-5 |
| 2003-05-26 | Italy 2 4 | SF | clay | Stefano Cobolli | 6-4 4-6 7-6(4) |
| 1999-08-21 | Italy 3 Masters 1 | R32 | clay | Stefano Cobolli | 7-6 7-6 |
| 1999-06-07 | Italy F11 | R16 | clay | Stefano Cobolli | 7-6 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.