Stefano Cobolli defeated Vincenzo Santopadre 2-6 6-3 6-4 in the Italy 8 4 semi-final on hard. The upset overturned the form book — Vincenzo Santopadre came in leading the head-to-head 2–0. Stefano Cobolli claimed a first win over Vincenzo Santopadre in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-03-03 | Italy 1 4 | R16 | clay | Vincenzo Santopadre | 7-6(1) 6-4 |
| 2002-10-28 | Italy 8 1 | SF | hard | Vincenzo Santopadre | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.