Matteo Cecchetti defeated Massimo Bertolini 6-3 4-6 6-3 in the Italy 5 Masters 4 round of 16 on clay. The upset overturned the form book — Massimo Bertolini came in leading the head-to-head 1–0. Matteo Cecchetti claimed a first win over Massimo Bertolini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-08-02 | Italy 5 Masters 2 | R32 | clay | Massimo Bertolini | 7-5 7-6 |