Stefano Cobolli defeated Andrea Grasselli 6-0 6-3 in the Italy 4 Masters 3 round of 16 on clay. The upset overturned the form book — Andrea Grasselli came in leading the head-to-head 2–0. Stefano Cobolli claimed a first win over Andrea Grasselli in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-08-03 | Italy 4 Masters 2 | R32 | clay | Andrea Grasselli | 4-6 6-1 6-2 |
| 1996-06-29 | Italy 3 Masters 4 | R32 | clay | Andrea Grasselli | 7-6 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.