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