Stefano Cobolli defeated Elia Grossi 2-6 6-4 6-1 in the Italy 3 Masters 4 qualifying round on clay. The upset overturned the form book — Elia Grossi came in leading the head-to-head 8–1. Stefano Cobolli narrowed the head-to-head to 8–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-05-28 | Italy F5 | R32 | clay | Elia Grossi | 7-6(2) 4-6 7-6(3) |
| 2000-06-19 | Italy 3 1 | QF | clay | Stefano Cobolli | 7-5 6-4 |
| 1998-11-07 | Egypt 2 Masters 2 | QF | hard | Elia Grossi | 6-4 6-7 6-4 |
| 1998-11-07 | Egypt 2 Masters 1 | R16 | hard | Elia Grossi | 6-4 6-2 |
| 1997-06-28 | Italy 4 Masters 4 | SF | clay | Elia Grossi | 0-6 6-3 7-5 |
| 1997-05-31 | Italy 3 Masters 2 | SF | clay | Elia Grossi | 6-1 6-2 |
| 1997-05-31 | Italy 3 Masters 4 | R32 | clay | Elia Grossi | 6-4 6-1 |
| 1997-05-31 | Italy 3 Masters 1 | QF | clay | Elia Grossi | 7-6 6-1 |
| 1997-04-05 | Italy 2 Masters 2 | R32 | clay | Elia Grossi | 3-6 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.