Andrea Grasselli defeated Stefano Cobolli 7-6 4-6 6-4 in the Italy 3 Masters 4 round of 32 on clay. Andrea Grasselli extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-06-28 | Italy 4 Masters 3 | R16 | clay | Stefano Cobolli | 6-0 6-3 |
| 1996-08-03 | Italy 4 Masters 2 | R32 | clay | Andrea Grasselli | 4-6 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.