Alessandro Tombolini defeated Giancarlo Petrazzuolo 4-6 6-0 6-3 in the Italy F15 round of 16 on clay. The upset overturned the form book — Giancarlo Petrazzuolo came in leading the head-to-head 1–0. Alessandro Tombolini claimed a first win over Giancarlo Petrazzuolo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-11 | Italy 1 Masters 1 | R32 | clay | Giancarlo Petrazzuolo | 6-0 2-6 7-6(5) |