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