Andrea Grasselli defeated Marco Danelli 6-4 1-6 6-3 in the Italy 4 Masters 4 round of 32 on clay. The upset overturned the form book — Marco Danelli came in leading the head-to-head 1–0. Andrea Grasselli claimed a first win over Marco Danelli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 3 | R32 | clay | Marco Danelli | 4-6 6-0 7-6 |