Nicolas Kischkewitz defeated Massimo Bertolini 6-1 6-2 in the Italy 5 Masters 1 qualifying round on clay. Nicolas Kischkewitz extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 4 | R32 | clay | Nicolas Kischkewitz | 6-2 6-2 |
| 1994-07-30 | Italy 3 Masters 2 | SF | clay | Massimo Bertolini | 6-2 6-2 |