Massimo Bertolini defeated Matteo Cecchetti 7-5 7-6 in the Italy 5 Masters 2 round of 32 on clay. The upset overturned the form book — Matteo Cecchetti came in leading the head-to-head 1–0. Massimo Bertolini claimed a first win over Matteo Cecchetti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-08-02 | Italy 5 Masters 4 | R16 | clay | Matteo Cecchetti | 6-3 4-6 6-3 |