Stefano Cobolli defeated Charles Edouard Maria 6-0 2-6 6-1 in the Italy F1 round of 32 on clay. The upset overturned the form book — Charles Edouard Maria came in leading the head-to-head 2–1. Stefano Cobolli narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-31 | Italy F9 | QF | clay | Charles Edouard Maria | 1-4 4-0 4-5(4) 4-2 5-4(4) |
| 1999-05-31 | Italy F10 | QF | clay | Stefano Cobolli | 6-3 6-0 |
| 1999-05-25 | Italy F9 | R32 | clay | Charles Edouard Maria | 6-3 6-4 |