Stefano Cobolli defeated Marco Monnecchi 6-2 7-6 in the Italy 3 Masters 4 round of 32 on clay. The result followed the form book — Stefano Cobolli came in leading the head-to-head 2–0. Stefano Cobolli extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Italy F1 | SF | clay | Stefano Cobolli | 6-4 6-1 |
| 1997-08-02 | Italy 5 Masters 1 | R32 | clay | Stefano Cobolli | 2-6 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.