Giancarlo Petrazzuolo defeated Alessandro Tombolini 6-0 2-6 7-6 in the Italy 1 Masters 1 round of 32 on clay. The upset overturned the form book — Alessandro Tombolini came in leading the head-to-head 1–0, but Giancarlo Petrazzuolo had been the form player, winning 3 of their last 6 on clay. Giancarlo Petrazzuolo claimed a first win over Alessandro Tombolini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Italy F15 | R16 | clay | Alessandro Tombolini | 4-6 6-0 6-3 |