Vincenzo Santopadre defeated Stefano Cobolli 6-3 6-1 in the Italy 8 1 semi-final on hard. Vincenzo Santopadre extended 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 4 | SF | hard | Stefano Cobolli | 2-6 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.