Massimo Bertolini defeated Nicolas Kischkewitz 6-2 6-2 in the Italy 3 Masters 2 semi-final on clay. The upset overturned the form book — Nicolas Kischkewitz came in leading the head-to-head 2–0. Massimo Bertolini claimed a first win over Nicolas Kischkewitz in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-08-02 | Italy 5 Masters 1 | QF | clay | Nicolas Kischkewitz | 6-1 6-2 |
| 1996-04-06 | Italy 1 Masters 4 | R32 | clay | Nicolas Kischkewitz | 6-2 6-2 |